Ammonium formate → HCID 89908187、化合物

HRID 525741ノート

反応式

HRID 525741 の反応式
[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

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 89906624HCID 89906624、化合物

生成物 1

HCID 89908187HCID 89908187、化合物

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fb205ee7b634415180f51b62bd4762e4
出典データセット
uspto-grants-2016_05
特許番号
US09340537B2

反応ノート

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