Ammonium Chloride → 7-Chloro-1-{[(1R,2R,4R)-4-hydroxy-2-methylcyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

HRID 1971009노트

반응식

HRID 1971009 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:14]([NH:15][C@@H:16]4[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][C@H:17]4[CH3:23])=[N:13][CH:12]=[C:11]([C:24]#[N:25])[C:7]=3[NH:8][C:9]=2[CH:10]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[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])=[N:13][CH:12]=[C:11]([C:24]#[N:25])[C:7]=3[NH:8][C:9]=2[CH:10]=1

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 686696457-Chloro-1-{[(1R,2R)-2-methyl-4-oxocyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

생성물 1

HCID 686692267-Chloro-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 7-chloro-1-{[(1R,2R)-2-methyl-4-oxocyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile (121 mg, 0.34 mmol) in MeOH (20 mL) was added sodium borohydride (26 mg, 0.69 mmol) at 0° C. The reaction mixture was left to stir for 30 min, 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 (C19H19ClN4O) [M+H]+, 355.1. found 355.0.

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-480bd76f2ac940f0b806e58c039fbf9b
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431569B2

반응 노트

불러오는 중…