Sodium sulfate decahydrate → HCID 86724130, compound

Participants

Reaction Steps

3-(4-Bromophenyl)-3-(5-((tert-butoxycarbonyl)amino)-1-ethyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)propanoic acid (0.786 g, 1.525 mmol, prepared using W from 4-bromobenzaldehyde, X from 1-ethyl-3-(pyridin-2-yl)-1H-pyrazol-5-amine then Y) was added in one portion to a mixture of LAH (0.232 g, 6.10 mmol) and Et2O (15.0 mL) under N2 at about 0° C. After about 1 h, the ice bath was removed. After stirring at rt for about 3 h, LAH (0.116 g, 3.05 mmol) was added in one portion. After about 2 h, the mixture was cooled to about 0° C. Sodium sulfate decahydrate was slowly added over about 15 min. After about 15 min, the ice bath was removed, the mixture was diluted with Et2O (20 mL), and then the mixture was left to vigorously stir for about 63 h. The mixture was filtered rinsing with Et2O (100 mL). The organic volatiles were removed under reduced pressure. The residue was purified on silica gel using a gradient of 50-75% EtOAc in heptane. The fractions containing product were combined and concentrated under reduced pressure to afford tert-butyl (4-(1-(4-bromophenyl)-3-hydroxypropyl)-1-ethyl-3-(pyridin-2-yl)-1H-pyrazol-5-yl)carbamate (0.359 g, 0.715 mmol, 47%) as a very pale yellow film. LC-MS (Table 1, Method g) Rt=2.45 min; m/z 501 and 503 (M+H)+; 1H NMR (400 MHz, DMSO) 8.82 (s, 1H), 8.59-8.52 (m, 1H), 7.89-7.72 (m, 2H), 7.39-7.18 (m, 5H), 5.02-4.87 (m, 1H), 4.61-4.45 (m, 1H), 3.97-3.86 (m, 2H), 3.36-3.22 (m, 1H), 2.36-2.04 (m, 2H), 1.43 (s, 9H), 1.43-1.21 (m, 3H).

Provenance & Evidence