Sodium borohydride → HCID 22614977, compound

HRID 843173Notes

Reaction equation

HRID 843173 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([N:7]=[CH:8][C:9]2[O:10][C:11]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:31])[CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[C:12]=3[C:13]=2[CH3:14])[CH:3]=1.[BH4-].[Na+]>CO>[CH3:1][C:2]1[O:6][N:5]=[C:4]([NH:7][CH2:8][C:9]2[O:10][C:11]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:31])[CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[C:12]=3[C:13]=2[CH3:14])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22615088HCID 22615088, compound

Product 1

HCID 22614977HCID 22614977, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (5-methyl-isoxazol-3-yl)-{3-methyl-4-[3-(methyl-pyridin-3-ylmethyl-amino)-propoxy]-benzofuran-2-ylmethylene}-amine (46 mg) in methanol (2 ml) was added sodium borohydride (20 mg) at room temperature. After 1 hour the mixture was concentrated in vacuo and purified by silica gel column chromatography developed by dichloromethane and methanol to give the titled compound as white solids (28 mg). ESI-MS: m/z 421 (MH+); 1H-NMR (CDCl3): δ 1.97-2.06 (2H, m), 2.25 (3H, s), 2.27 (3H, s), 2.28 (3H, s), 2.59 (2H, t, J=6.9 Hz), 3.52 (2H, s), 4.09 (2H, t, J=5.94 Hz), 4.41 (2H, s), 5.53 (1H, s), 6.58 (1H, d, J=7.6 Hz), 7.00 (1H, d, J=7.6 Hz), 7.05-7.15 (2H, m), 7.59-7.63 (1H, m), 8.39 (1H, dd, J=1.7 Hz, 4.9 Hz), 8.49 (1H, d, J=2.0 Hz).

Workup

  1. concentrationAfter 1 hour the mixture was concentrated in vacuo
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-09fb89491dc94973bb87dbfd82e10d3a
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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