Ammonium formate → HCID 89908187, 화합물

HRID 525741노트

반응식

HRID 525741 반응식
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:26]([C:27]3[N:28](CC4C=CC(OC)=CC=4)[C:29]([CH3:32])=[CH:30][N:31]=3)=[CH:25][C:10]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)=[O:12])=[CH:9][N:8]=2)[CH2:3]1.C([O-])=O.[NH4+]>[Pd].CCO>[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:26]([C:27]3[NH:28][C:29]([CH3:32])=[CH:30][N:31]=3)=[CH:25][C:10]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:22])[F:23])=[CH:16][CH:15]=3)=[O:12])=[CH:9][N:8]=2)[CH2:3]1

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 89906624HCID 89906624, 화합물

생성물 1

HCID 89908187HCID 89908187, 화합물

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

Palladium on carbon 10% (5.63 mg) was added to a stirred mixture of (R)-6-(3-hydroxypyrrolidin-1-yl)-5-(1-(4-methoxybenzyl)-5-methyl-1H-imidazol-2-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 72.1, 300 mg, 0.053 mmol) and ammonium formate (33 mg, 0.529 mmol) in EtOH (5 mL) and the mixture was heated under reflux for 52 h. The RM was filtered through Hyflo® and the solvent was evaporated off under reduced pressure to give the crude product which was purified by SFC (Column DEAP, from 21% to 26% in 10 min) to afford the title compound as an amorphous solid. HPLC (Condition 4) tR=4.01 min, UPLC-MS (Condition 8) tR=0.76 min, m/z=448.2 [M+H]+; 1H-NMR (600 MHz, DMSO-d6) δ ppm 1.66-1.92 (m, 2H), 2.11-2.29 (m, 2H), 2.91 (br.s, 1H), 3.28 (br.s, 2H), 3.38-3.50 (m, 2H), 4.22 (br. s, 1H), 4.89 (br.s, 1H), 6.63-6.74 (m, 1H), 6.87-6.96 (m, 1H), 7.35 (d, J=8.59 Hz, 2H), 7.88 (d, J=8.92 Hz, 2H), 8.12 (s, 1H), 8.77 (s, 1H), 10.22 (s, 1H), 11.85-12.17 (m, 1H).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 52 h
  3. filtrationThe RM was filtered through Hyflo®
  4. customthe solvent was evaporated off under reduced pressure
  5. customto give the crude product which
  6. customwas purified by SFC (Column DEAP, from 21% to 26% in 10 min)

출처 및 근거

ORD 기록
ord-fb205ee7b634415180f51b62bd4762e4
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340537B2

반응 노트

불러오는 중…