Sodium borohydride → HCID 57444325, compound

HRID 734556Notes

Reaction equation

[BH4-].[Na+].[CH3:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[N:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]([C:23]3[CH:24]=[C:25]([NH:29][C:30](=[O:32])[CH3:31])[CH:26]=[CH:27][CH:28]=3)=[O:22])[CH2:16][CH2:15]2)[N:5]=1>C(Cl)Cl>[OH:22][CH:21]([C:23]1[CH:24]=[C:25]([NH:29][C:30](=[O:32])[CH3:31])[CH:26]=[CH:27][CH:28]=1)[CH2:20][N:17]1[CH2:18][CH2:19][N:14]([C:10]2[CH:9]=[CH:8][CH:7]=[C:6]3[C:11]=2[CH:12]=[CH:13][C:4]([CH3:3])=[N:5]3)[CH2:15][CH2:16]1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium borohydride (0.015 g, 1.6 eq) was added to a stirred solution of N-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]acetyl}phenyl)acetamide (0.102 g, 1 eq) in dry DCM (2 mL) cooled to 0° C. under an inert atmosphere. The reaction was warmed to room temperature and stirred for 18 hours. The mixture was diluted with DCM (10 mL) and washed with water (2×10 mL). The organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure. The crude material was purified on SPE cartridge (Silica) using as eluant DCM-methanol (97:3), affording the title compound in 42% yield (0.104 g).

Workup

temperatureThe reaction was warmed to room temperature
washwashed with water (2×10 mL)
dry with materialThe organic phase was dried over sodium sulfate
customthe solvent was removed under reduced pressure
customThe crude material was purified on SPE cartridge (Silica)

Sources & evidence

ORD record: ord-cd4a2b49a5f847f18b8b81db9318f927
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592346B2

Reaction notes

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