Category: 923591-51-9

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.923591-51-9,5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.,923591-51-9

Step 1 : 5-Bromo-N-(thiazol-2-yl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide A solution of imidazole (1.530 g, 22.47 mmol) and thiazol-2 -amine (0.750 g, 7.49 mmol) in 8 mL DCM was cooled to -78 C and was treated with sulfuryl chloride (0.609 ml, 7.49 mmol). After stirring for 20 minutes, the cooling bath was removed and the reaction mixture was allowed to stir for an additional 30 minutes. 5-Bromo-l,2,3,4- tetrahydroisoquinoline hydrochloride (ASW Medchem, Brunswick, NJ, 1.396 g, 5.62 mmol) was added, followed by triethylamine (7.31 ml, 52.4 mmol). The reaction mixture was then heated to 80 C for 30 minutes. The mixture was cooled to rt and poured into IN citric acid solution before being extracted into EtO Ac. The organics were dried over MgS04 and concentrated. Purification of the residue by silica gel column chromatography (0 to 100% EtO Ac/heptane) gave 5-bromo-N-(thiazol-2-yl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide (1.092 g, 2.92 mmol). [M+H]+ = 375.6.

As the paragraph descriping shows that 923591-51-9 is playing an increasingly important role.

Reference£º
Patent; AMGEN INC.; DINEEN, Thomas; KREIMAN, Charles; WEISS, Matthew; GEUNS-MEYER, Stephanie; WO2013/134518; (2013); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

923591-51-9, 5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,923591-51-9

2-Acetyl-5-bromo-l,2,3,4-tetrahydroisoquinoline5-Bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (2.0 g, 8.0 mmol) was taken up in diethyl ether (20 mL) and washed with NaOH (aq, IN), dried (Na2SO4) and concentrated to give the free amine (1.67 g) that was dissolved in pyridine (15 mL) and cooled to 0 0C. Acetic anhydride (0.82 mL, 8.7 mmol) was added dropwise and the reaction was stirred at RT overnight. Azeotropic evaporation with toluene several times gave the product as a white solid (1.9 g, 94%).1H NMR (SOO MHz, DMSO-d6): delta 7.53 – 7.46 (m, IH), 7.27 – 7.11 (m, 2H), 4.66 and 4.61 rotamers 4:6 (s, 2H), 3.73 – 3.66 (m, 2H), 2.83 and 2.71 rotamers 6:4 (t, J= 6.1 Hz, 2H), 2.09 and 2.07 rotamers 6:4 (s, 3H); APCI-MS m/z: 254/256 1:1 [MH+].

The synthetic route of 923591-51-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/7747; (2009); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.923591-51-9,5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,as a common compound, the synthetic route is as follows.,923591-51-9

Example 62 : 5 -(3 ‘,4’-difluoro-3 -methoxy- [1, 1 ‘-biphenyl] -4-yl)-N-( 1 ,3 ,4-thiadiazol-2-yl)-3 ,4- dihydroisoquinoline-2( 1 H)-sulfonamide Step 1 : 5-bromo-N-(l,3,4-thiadiazol-2-yl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide A solution of l, l”-sulfonyldiimidazole (0.588 g, 2.97 mmol) and l,3,4-thiadiazol-2- amine (0.300 g, 2.97 mmol) in 6 mL of DMF was cooled to 0C. NaH (60% in mineral oil) (0.238 g, 9.91 mmol) was added. After 30 minutes, the reaction mixture was heated to 80C for one hour. 5-bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (0.737 g, 2.97 mmol) and n,n-diisopropylethylamine (2.59 ml, 14.83 mmol) were added, and the reaction mixture was heated to 110C for an additional 3 hours. The reaction mixture was then diluted with DCM and washed with IN citric acid solution. The organics were dried over MgSC^ and concentrated. Purification of the crude residue by reverse phase column chromatography [Redisep Gold C18, 10-100% (0.1%NH4OH in MeOH)/(0.1%NH4OH in water)] gave 5- bromo-N-(l,3,4-thiadiazol-2-yl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide (0.520 g, 1.386 mmol, 46.7 % yield). (M+H)+= 375.0.

923591-51-9 5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride 45074003, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; AMGEN INC.; DINEEN, Thomas; KREIMAN, Charles; WEISS, Matthew; GEUNS-MEYER, Stephanie; WO2013/134518; (2013); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

923591-51-9, 5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,923591-51-9

Intermediate O: 5-(2-(l-Methyl-lH-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-l,2,3,4- tetrahydroisoquinoline A vial was charged with 5-bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (ASW Medchem, Brunswick, NJ, 400.42 mg, 1.367 mmol), (2-(l- methyl-lH-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)boronic acid (Intermediate B, 443 mg, 1.640 mmol), potassium phosphate (1 160 mg, 5.47 mmol), and Pd(AmPhos)2Ci2 (Sigma- Aldrich, St. Louis, MO, 48.4 mg, 0.068 mmol). The vial was flushed with Ar (g), then dioxane (2928 mu) and water (976 mu) were added in sequence. The mixture was heated in a microwave reactor for 30 min at 90 C. After cooling to room temperature, the mixture was diluted with EtOAc, washed with water (and a small amount of brine to break up emulsions, 2x), washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was taken up in MeOH, then loaded onto a 10 g SCX-2 ion exchange column. The column was eluted with MeOH, then with 2M ammonia in MeOH. The basic filtrate was concentrated, and the residue was chromatographed on a 40 g silica gel column with 0 to 10% MeOH/DCM to provide 5-(2-(l -methyl- lH-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-l ,2,3,4- tetrahydroisoquinoline as a pale yellow solid. [M+H]+ = 358.1. XH NMR (400 MHz, DMSO-d6) delta ppm = 7.91 – 7.80 (m, 2 H), 7.56 (d, J= 8.0 Hz, 1 H), 7.28 (d, J= 2.0 Hz, 1 H), 7.09 – 6.95 (m, 2 H), 6.84 (dd, J= 1.3, 7.4 Hz, 1 H), 5.96 (d, J= 1.9 Hz, 1 H), 3.85 (s, 2 H), 3.52 (br. s., 3 H), 2.93 – 2.84 (m, 1 H), 2.79 – 2.67 (m, 1 H), 2.48 – 2.39 (m, 1 H), 2.09 (td, J= 5.3, 16.7 Hz, 1 H).

923591-51-9 5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride 45074003, atetrahydroisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; AMGEN INC.; DINEEN, Thomas; KREIMAN, Charles; WEISS, Matthew; GEUNS-MEYER, Stephanie; WO2013/134518; (2013); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

923591-51-9, 5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,923591-51-9

Intermediate AA: 5-Bromo-N-(l,2,4-thiadiazol-5-yl)-3,4-dihydroisoquinoline-2(lH)- sulfonamide To a 50 mL flask containing sodium l,2,4-thiadiazol-5-ylsulfamate (Intermediate A, 96 mg, 0.472 mmol) and 10 mL of DCM was added PC15 (Aldrich, St. Louis, MO, 245 mg, 1.179 mmol). The resutling slurry was heated at 50 C for 1.5 hours. LCMS showed conversion to the methyl sulfamate (following quench into methanol). The reaction was cooled to rt and was quenched with the addition of 5 drops of brine. The resulting slurry was stirred vigorously for 5 minutes before being filtered through a plug of diatomaceous earth, washing well with DCM. The mixture was concentrated under reduced pressure. The derived oil was taken up in 1 mL of DCM and was added to a solution of 5-bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (ASW Medchem, 50 mg, 0.236 mmol) and TEA (164 mu, 1.179 mmol) in 2 mL of DCM at 0 C. Another 0.164 mL of TEA was added and the reaction allowed to warm to room temeprature where it was maintained for 2 hours. LCMS showed clean conversion to sulfonamide. The reaction was allowed to stir overnight before being diluted with saturated sodium bicarbonate (10 mL) and poured into a separatory funnel containing methylenechloride (10 mL). The layers were separated and the aqueous layer was extracted with methylenechloride (2 x 25 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under a vacuum to provide a yellow oil that was purified by silica gel chromatography (Redi-Sep pre-packed silica gel column (12 g), 0-10% methanol in methylenechloride) to provide 5-bromo-N-(l,2,4-thiadiazol-5-yl)-3,4- dihydroisoquinoline-2(lH)-sulfonamide as an off white solid. [M+H]+ = 375.0 XH NMR (400 MHz, Acetone)8 ppm 8.28 (s, 1H), 7.96 (s, 1H), 7.45 – 7.50 (m, 1H), 7.09 – 7.20 (m, 2H), 4.32 (s, 2H), 3.48 (t, J = 6.1 Hz, 2H), 2.86 – 2.92 (m, 2H)

As the paragraph descriping shows that 923591-51-9 is playing an increasingly important role.

Reference£º
Patent; AMGEN INC.; DINEEN, Thomas; KREIMAN, Charles; WEISS, Matthew; GEUNS-MEYER, Stephanie; WO2013/134518; (2013); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem