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

HRID 1971009Notes

Reaction equation

HRID 1971009 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 686692267-Chloro-1-{[(1R,2R,4R)-4-hydroxy-2-methylcyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-480bd76f2ac940f0b806e58c039fbf9b
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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