Sodium borohydride → 2-[4-[5-[(1,5-Dimethylpyrazol-3-yl)amino]-1-methyl-6-oxo-3-pyridyl]-3-(hydroxymethyl)-2-pyridyl]-10-fluoro-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-1-one

HRID 593014ノート

反応式

HRID 593014 の反応式
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([NH:8][C:9]2[C:14](=[O:15])[N:13]([CH3:16])[CH:12]=[C:11]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([N:23]4[CH2:35][CH2:34][C:33]5[N:32]6[C:27]([CH2:28][CH2:29][CH2:30][CH2:31]6)=[C:26]([F:36])[C:25]=5[C:24]4=[O:37])[C:18]=3[CH:38]=[O:39])[CH:10]=2)=[N:3]1.[BH4-].[Na+]>CO>[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([NH:8][C:9]2[C:14](=[O:15])[N:13]([CH3:16])[CH:12]=[C:11]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([N:23]4[CH2:35][CH2:34][C:33]5[N:32]6[C:27]([CH2:28][CH2:29][CH2:30][CH2:31]6)=[C:26]([F:36])[C:25]=5[C:24]4=[O:37])[C:18]=3[CH2:38][OH:39])[CH:10]=2)=[N:3]1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 866844934-{5-[(1,5-Dimethyl-1H-pyrazol-3-yl)amino]-1-methyl-6-oxo-1,6-dihydro pyridin-3-yl}-2-{10-fluoro-1-oxo-1H,2H,3H,4H,6H,7H,8H,9H-pyrido[3,4-b]indolizin-2-yl}pyridine-3-carbaldehyde

生成物 1

HCID 866844942-[4-[5-[(1,5-Dimethylpyrazol-3-yl)amino]-1-methyl-6-oxo-3-pyridyl]-3-(hydroxymethyl)-2-pyridyl]-10-fluoro-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-1-one収率 52%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 261a (90.0 mg, 0.17 mmol) in methanol (5 mL) was added sodium borohydride (64.6 mg, 1.7 mmol) at room temperature. The reaction was stirred for 0.5 h. It was then quenched with water (2 mL) and evaporated in vacuo. The residue was extracted with dichloromethane (3×10 mL). The combined dichloromethane extract was concentrated under reduced pressure and the residue was purified by reverse-phase prep-HPLC to afford 261 (47.0 mg, 52%) as a white solid. MS-ESI: [M+H]+ 532.3. 1H NMR (500 MHz, DMSO-d6) δ 8.47 (d, J=5.0 Hz, 1H), 8.05 (s, 1H), 8.03 (d, J=2.5 Hz, 1H), 7.39 (d, J=2.5 Hz, 1H), 7.31 (d, J=5.0 Hz, 1H), 5.89 (s, 1H), 4.87-4.85 (m, 1H), 4.45-4.36 (m, 2H), 4.11-4.09 (m, 1H), 3.93-3.91 (m, 1H), 3.79-3.76 (m, 2H), 3.59 (s, 3H), 3.58 (s, 3H), 3.00-2.94 (m, 2H), 2.66-2.63 (m, 2H), 2.18 (s, 3H), 1.90-1.88 (m, 2H), 1.78-1.73 (m, 2H)

後処理

  1. customIt was then quenched with water (2 mL)
  2. customevaporated in vacuo
  3. extractionThe residue was extracted with dichloromethane (3×10 mL)
  4. extractionThe combined dichloromethane extract
  5. concentrationwas concentrated under reduced pressure
  6. customthe residue was purified by reverse-phase prep-HPLC

出典と根拠

ORDレコード
ord-03daec67bbea441eac6535f69df01ebc
出典データセット
uspto-grants-2016_01
特許番号
US09238655B2

反応ノート

読み込み中…