Introduction of a new synthetic route about 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

With the rapid development of chemical substances, we look forward to future research findings about 166591-85-1

2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid, cas is 166591-85-1, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

T3P (50% in EtOAc) (3.22 mL, 5.41 mmol) was added to a solution of 2-(/eri- butoxycarbonyl)-l,2,3,4-tetrahydroisoquinoline-l-carboxylic acid (1.00 g, 3.61 mmol),(trans)- l-methoxy-2,3-dihydro-1H-inden-2-amine (Intermediate 2, 0.647 g, 3.97 mmol) and TEA (0.754 mL, 5.41 mmol) in DCM (20 mL). The reaction was stirred at room temperature for 1.5 h. The mixture was partitioned between DCM and saturated NaHCCh, dried (phase separator) and concentrated in vacuo. The crude product was purified by column chromatography on silica, eluted with 0-50% EtOAc/petroleum ether to afford the title compound. ‘Eta NMR (300 MHz, DMSO-4s) delta ppm 1.34 – 1.50 (m, 9 H), 2.66 – 2.83 (m, 2 H), 2.94 – 3.09 (m, 1 H), 3.13 – 3.28 (m, 3 H), 3.34 – 3.39 (m, 1 H), 3.45 – 3.66 (m, 1 H), 3.82 – 3.96 (m, 1 H), 4.20 – 4.37 (m, 1 H), 4.60 – 4.74 (m, 1 H), 5.17 – 5.41 (m, 1 H), 7.13 – 7.37 (m, 7 H), 7.40 – 7.59 (m, 1 H), 8.57 – 8.80 (m, 1 H) (0622) MS ES+: 445 (M+Na), 166591-85-1

With the rapid development of chemical substances, we look forward to future research findings about 166591-85-1

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; LIWICKI, Gemma; MACK, Stephen; STEPHENSON, Anne; TEALL, Martin; WHITE, Kathryn; (168 pag.)WO2018/47983; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Downstream synthetic route of 42923-79-5

As the paragraph descriping shows that 42923-79-5 is playing an increasingly important role.

42923-79-5, 7-Nitro-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,42923-79-5

To a stifled solution of 7-nitro-i,2,3,4-tetrahydroisoquinoline (10 g, 56.18 mmol) in dry i,2-dichloroethane (200 mL) was added formalin (2.3 mL, 61.80 mmol, 37% aq. formaldehyde) followed by NaCNBH3 (52 g, 245.35 mmol). The reaction was stifled vigorously at RT for 24 h. The solvent was removed in vacuo, and the mixture was diluted with EA (200 mL). Sat. NaHCO3 (200 mL) was added with vigorous stifling. The layers were separated, and the water layer was extracted with ethyl acetate (2 x 100 mL). The combined organic layers were dried (Na2504) and concentrated in vacuo to give a brown oil. The crude product was purified by chromatography (5i02, MeOH/DCM) to afford mixture of 3-regio isomers (5 g, 26.04 1 mmol). The mixture of regioisomers (4 g) was purified by SFCPrep (Lux Amylose-2, (4.6 x 250 mm), 90% C02: 10% 0.5% DEA in ethanol) to afford 2- methyl-7-nitro- 1,2,3 ,4-tetrahydroisoquinoline (1.5 g). MS (ESI) m/z 193.0 [M+H] .

As the paragraph descriping shows that 42923-79-5 is playing an increasingly important role.

Reference£º
Patent; ZENO ROYALTIES & MILESTONES, LLC; HUANG, Peter, Qinhua; BOREN, Brant, Clayton; BUNKER, Kevin, Duane; LIU, Hui; PALIWAL, Sunil; (99 pag.)WO2019/28008; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Brief introduction of 78183-55-8

As the paragraph descriping shows that 78183-55-8 is playing an increasingly important role.

78183-55-8, (S)-Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

78183-55-8, D. (S)-1,2,3,4-Tetrahydro-2-[3-methyl-N-[(phenylmethoxy)carbonyl]-L-valyl]-3-isoquinolinecarboxylicacid, methyl ester To a solution of Compound C (5.31 g, 20 mmol) in dichloromethane (80 mL) at 0C under argon were sequentially added diisopropylethylamine (10.6 mL, 60 mmol), benzotriazol-1-yloxytris- (dimethylamino)phosphonium hexafluorophosphate (5.08 g, 20 mmol) and (S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, methyl ester, hydrochloride (5.68 g, 25 mmol). The reaction mixture was allowed to warm to 5C over 2 hours, and then stirred overnight (16 hours). The mixture was washed with 1N hydrochloric acid, saturated sodium bicarbonate and brine (50 mL each). The organic layer was dried (magnesium sulfate), filtered and concentrated to afford an oil. Purification by flash silica gel column chromatography eluding with 20% ethyl acetate in hexanes afforded Compound D (4.0 g, 45%).

As the paragraph descriping shows that 78183-55-8 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; EP618221; (1994); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Simple exploration of 226942-29-6

226942-29-6 6-Bromo-1,2,3,4-tetrahydroisoquinoline 15885183, atetrahydroisoquinoline compound, is more and more widely used in various.

226942-29-6, 6-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

226942-29-6, A mixture of 6-bromo-1 ,2,3,4-tetrahydroisoquinoline (2.86g, 12 mmol, Allichem LLC), zinc cyanide (1.76g, 15 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.33g, 1.2 mmol) in DMF (20ml) was split between two microwave vials and heated (microwave) for 60min at 1300C. The mixture was concentrated in vacuo and the residue dissolved in DCM and loaded onto a silica cartridge. The cartridge was eluted with a gradient of 2M ammonia in methanol / DCM (5-10%). The appropriate fractions were combined and evaporated in vacuo to give 1 ,2,3,4-tetrahydro-6- isoquinolinecarbonitrile (1.41 g) as a colourless solid. LCMS (Method formate): Retention time 0.36min, MH+ = 158

226942-29-6 6-Bromo-1,2,3,4-tetrahydroisoquinoline 15885183, atetrahydroisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; GLAXO GROUP LIMITED; BAILEY, James, Matthew; BIT, Rino, Antonio; DEMONT, Emmanuel, Hubert; HARRISON, Lee, Andrew; JONES, Katherine, Louise; SMETHURST, Christian, Alan, Paul; WITHERINGTON, Jason; WO2010/146105; (2010); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

New learning discoveries about 57196-62-0

As the paragraph descriping shows that 57196-62-0 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.57196-62-0,6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.,57196-62-0

6-Methoxy-1,2,4,4-tetrahydroisoquinoline hydrochloride (2.0 g, 10 mmol) and triethylamine (3.03 g, 30 mmol) were dissolved in dichloromethane (100 mL) Di-tert-butyl dicarbonate (2.62 g, 12 mmol) was added and reacted at room temperature for 2 hours. (50 mL), the organic phase was combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude product (3.0 g).

As the paragraph descriping shows that 57196-62-0 is playing an increasingly important role.

Reference£º
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd.; Wu Yongqian; (29 pag.)CN104876914; (2017); B;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Simple exploration of 170097-67-3

As the paragraph descriping shows that 170097-67-3 is playing an increasingly important role.

170097-67-3, 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,170097-67-3

Step 2: 3-amino-6-[2-(l-cyano-l-methyl-ethyl)-4-pyridyl]pyrazine-2- carbohydrazide (49.5 mg, 0.1665 mmol), 2-tert-butoxycarbonyl-3,4-dihydro-lH- isoquinoline-6-carboxylic acid (50.80 mg, 0.1832 mmol), diisopropyl ethyl amine (25.82 mg, 34.80 mu, 0.1998 mmol) and (benzotriazol-l-yloxy-dimethylamino-methylene)-dimethyl- ammonium tetrafluoroborate (58.82 mg, 0.1832 mmol) was stirred at ambient temperature in N,N-dimethyl formamide (495.0 mu) for 1 hour. The reaction mixture was partitioned between water and ethyl acetate. The combined organic extracts were washed with aqueous saturated sodium bicarbonate, then 0.5 N hydrochloric acid, followed by brine. The organic extracts were then dried over MgSC^ and concentrated in vacuo to give the sub-titled product. (92 mg, 99.27%) LC/MS m/z 557.2 [M+H]+.

As the paragraph descriping shows that 170097-67-3 is playing an increasingly important role.

Reference£º
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; MACCORMICK, Somhairle; STORCK, Pierre-Henri; PINDER, Joanne; O’DONNELL, Michael, Edward; KNEGTEL, Ronald Marcellus, Alphonsus; YOUNG, Stephen, Clinton Young; KAY, David; REAPER, Philip, Michael; DURRANT, Steven, John; TWIN, Heather, Clare; DAVIS, Christopher, John; WO2012/138938; (2012); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

New learning discoveries about 57196-62-0

As the paragraph descriping shows that 57196-62-0 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.57196-62-0,6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.,57196-62-0

A mixture of 5-bromo-2-pyrimidin-2-yl-pyrimidine (100 mg, 422 muiotaetaomicron, the product of step 3 in Example 1), 6-methoxy-l,2,3,4-tetrahydroisoquinoline hydrochloride (84.2 mg, 422 muiotaetaomicron), Pd2(dba)3 (386 mg, 422 muiotaetaomicron), Ruphos (197 mg, 422 muiotaetaomicron) and sodium ie/t-butoxide (40.5 mg, 422 muiotaetaomicron) in toluene (5 mL) was heated at 100 C with stirring for 2 hrs under N2. The reaction mixture was diluted with H20 and extracted with EA (30 mL) for three times. The combined organic layer was dried over Na2S04 and concentrated in vacuo. The residue was purified by pre- HPLC to give 6-methoxy-2-(2-pyrimidin-2-ylpyrimidin-5-yl)-3,4-dihydro-lH-isoquinoline (3 mg) as light yellow solid. lH NMR (400 MHz, CDCI3) delta ppm: 3.05 (t, 2 H), 3.52 (s, 2 H), 3.73 (t, 2 H), 3.82 – 3.86 (m, 3 H), 4.55 (s, 2 H), 6.78 (d, 1 H), 6.84 (dd, 1 H), 7.18 (d, 1 H), 7.35 (br. s., 1 H), 8.51 – 8.68 (m, 2 H), 8.92 – 9.05 (m, 2 H).

As the paragraph descriping shows that 57196-62-0 is playing an increasingly important role.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (81 pag.)WO2018/83136; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Simple exploration of 42923-77-3

42923-77-3 6-Methoxy-1,2,3,4-tetrahydroisoquinoline 39356, atetrahydroisoquinoline compound, is more and more widely used in various.

42923-77-3, 6-Methoxy-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,42923-77-3

Under a nitrogen atmosphere, 0.5 g of 6-methoxy-1,2,3,4-tetrahydroisoquinoline was added to 20 mL of DMF in a flask and stirred to dissolve, and then 1.1 g of cesium carbonate was added at room temperature. After 30 minutes, 1.0 g of (S)-ethyl 3-(4-(4-(2-(methylsulfonyloxy)ethyl)benzyloxy)phenyl)hex-4-ynoate prepared in Preparative Example 16 was added dropwise, followed by stirring at room temperature for 12 hours. Upon completion of the reaction, distilled water was slowly added dropwise, extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate, and then concentrated. Thereafter, the reaction product was separated by silica column chromatography to give the title compound. 1H NMR (400MHz, CDCl3):delta 7.35(2H,d), 7.30(2H,d), 7.23(2H,d), 7.00(1H,d), 6.85(2H,d), 6.80(1H,d), 6.70(1H,d), 5.00(2H,s), 4.30(2H,m), 4.13(2H,m) 4.03(1H,t), 3.80(3H,s), 3.58(6H,m), 3.30(2H,s), 2.78(2H,m), 1.86(3H,d), 1.28(3H,m).

42923-77-3 6-Methoxy-1,2,3,4-tetrahydroisoquinoline 39356, atetrahydroisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; Hyundai Pharm Co., Ltd.; YANG, Jin; KIM, Jin Woong; LEE, Han Kyu; KIM, Jae Hyun; SON, Chang Mo; LEE, Kyu Hwan; CHOI, Hyung-Ho; KIM, Daehoon; HA, Tae-Young; RHEE, Jaekeol; (94 pag.)EP3207928; (2017); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Brief introduction of 877861-62-6

As the paragraph descriping shows that 877861-62-6 is playing an increasingly important role.

877861-62-6, Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

877861-62-6, Step 1 : Preparation of 2-(1 ,1-dimethylethyl) 6-methyl 3,4-dihvdro-2,6(1/-/)-isoquinoline- dicarboxylate; To a solution of methyl 1 ,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride(0.30 g, 1.32 mmol) in dioxane/H2O (2:1 , 5 ml.) was added 1 N NaOH (1.97 ml_, 1.97 mmol) followed by BoC2O (0.43 g, 1.97 mmol). The reaction was stirred at room temperature for 1 hour, at which time LCMS indicated complete conversion to product.The reaction was poured into H2O (10 ml.) and extracted with CH2CI2 (3×10 ml_). The organics were dried (Na2SO4) and evacuated. The crude carbamate was used directly in the next step.

As the paragraph descriping shows that 877861-62-6 is playing an increasingly important role.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/49154; (2009); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Introduction of a new synthetic route about 67123-97-1

With the rapid development of chemical substances, we look forward to future research findings about 67123-97-1

1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, cas is 67123-97-1, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.,67123-97-1

A solution of chiral monomer 5 [(R)- and (R)-1,2,3,4-tetrahydroisoquinoline-3- carboxylic acid] (4.27 g, 20 mmol) in methanol (20 mL) was cooled to 0 C, and added drop wise with 5.2 mL thionyl chloride. The reaction mixture was stirred for overnight at ambient temperature. The solvent was removed by rotary evaporator under vacuum to give compound 6 (5.29 g), yield: 94.4%. 1H NMR (300 MHz, D2O, r.t.) delta 7.45-7.24 (m, 4H), 4.60 (d, J = 5.5 Hz, 1H), 4.56 (d, J = 5.4 Hz, 1H), 4.53 (br s, 1H), 3.93 (s, 3H), 3.53 (dd, J = 17.4, 5.5 Hz, 1H), 3.53 (dd, J = 17.4, 5.5 Hz, 1H), 3.32 (dd, J = 17.3, 10.9 Hz, 1H), 3.32 (dd, J = 17.3, 10.9 Hz, 1H). HR ESIMS: m/z 192.1028 [M + H]+ (calcd. 192.1025).

With the rapid development of chemical substances, we look forward to future research findings about 67123-97-1

Reference£º
Article; Liang, Chuanpeng; Hao, Huilin; Wu, Xingkang; Li, Zhenyu; Zhu, Jing; Lu, Chunhua; Shen, Yuemao; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 272 – 282;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem