Ammonium Chloride → 8-Fluoro-1-{[(1R,2R,4R)-4-hydroxy-2-methylcyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

HRID 1971017노트

반응식

HRID 1971017 반응식
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]([C:24]#[N:25])=[CH:12][N:13]=[C:14]([NH:15][C@@H:16]4[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][C@H:17]4[CH3:23])[C:5]=3[C:4]=2[CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO.[Cl-].[Na+].O>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]([C:24]#[N:25])=[CH:12][N:13]=[C:14]([NH:15][C@@H:16]4[CH2:21][CH2:20][C@@H:19]([OH:22])[CH2:18][C@H:17]4[CH3:23])[C:5]=3[C:4]=2[CH:3]=1

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 686689758-Fluoro-1-{[(1R,2R)-2-methyl-4-oxocyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

생성물 1

HCID 686691058-Fluoro-1-{[(1R,2R,4R)-4-hydroxy-2-methylcyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

시약·촉매·용매 2

HCID 887Methanol용매HCID 57417360Sodium chloride; water용매

실험 절차

To a stirred solution of 8-fluoro-1-{[(1R,2R)-2-methyl-4-oxocyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile (7.23 g, 21.5 mmol) in MeOH (100 mL) was added sodium borohydride (1.63 g, 43.0 mmol) at 0° C. The reaction mixture was left to stir at room temperature for 1 h, treated with aqueous ammonium chloride and brine, and extracted with EtOAc. The combined organics were dried (sodium sulfate), and concentrated. The diastereomers were separated by flash chromatography to afford the title compound. LRMS (APCI) calc'd for (C19H19FN4O) [M+H]+, 339.2. found 339.1.

후처리

  1. waitThe reaction mixture was left
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organics were dried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe diastereomers were separated by flash chromatography

출처 및 근거

ORD 기록
ord-531337469df14da28b7a64704185f952
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431569B2

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