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

HRID 1971017Notes

Reaction equation

HRID 1971017 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 686691058-Fluoro-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 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.

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-531337469df14da28b7a64704185f952
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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