Sodium borohydride → HCID 52914256, compound

HRID 341036Notes

Reaction equation

HRID 341036 reaction equation
[F:1][C:2]1[C:11]2[N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH:23]=[CH:22][CH:21]=[N:20]4)=[CH:15][CH:14]=3)[CH:9]=[C:8]3[C:24](=[O:35])[N:25]([C:27]4[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=4[CH:29]=[O:30])[N:26]=[C:7]3[C:6]=2[C:5]([F:36])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[C:11]2[N:10]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([N:19]4[CH:23]=[CH:22][CH:21]=[N:20]4)=[CH:17][CH:18]=3)[CH:9]=[C:8]3[C:24](=[O:35])[N:25]([C:27]4[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=4[CH2:29][OH:30])[N:26]=[C:7]3[C:6]=2[C:5]([F:36])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86668674HCID 86668674, compound

Product 1

HCID 52914256HCID 52914256, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(6,9-Difluoro-3-oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)benzaldehyde [(Example 39) 15 mg, 0.31 mmol] was dissolved in methanol (3 mL), treated with sodium borohydride (4 mg, 0.62 mmol, 2 equiv) and stirred at ambient temperature for 2 hours. The mixture was concentrated in vacuo and the residue was purified by silica gel gradient chromatography (100:0 to 80:20; dichloromethane:methanol), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 8.46 (1H, s), 7.91 (1H, d, J=2.5 Hz), 7.75-7.70 (3H, m), 7.56 (1H, dd, J=7.3, 1.3 Hz), 7.45 (1H, td, J=7.6, 1.5 Hz), 7.38 (1H, td, J=7.4, 1.4 Hz), 7.30-7.17 (5H, m), 6.48 (1H, dd, J=2.4, 1.7 Hz), 5.66 (1H, d, J=2.4 Hz), 4.52 (2H, br s) ppm; high resolution mass spectrometry (ES+) m/z 484.1567 [(M+H)+; calculated for C27H20F2N5O2: 484.1580].

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by silica gel gradient chromatography (100:0 to 80:20; dichloromethane:methanol)

Sources & evidence

ORD record
ord-91298740bd634bb9949c378550853bab
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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