Sodium borohydride → N-(4-(2-(Benzhydrylamino)-3-chloropyridin-4-yloxy)-3-fluorophenyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxamide

HRID 2380954Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N:33]=[C:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[C:23](=[O:24])[C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:21][NH:20][CH:19]=2)=[O:17])=[CH:11][C:10]=1[F:32].[BH4-].[Na+]>CCO.C1COCC1>[CH:34]([NH:33][C:3]1[C:2]([Cl:1])=[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]3[C:23](=[O:24])[C:22]([C:25]4[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=4)=[CH:21][NH:20][CH:19]=3)=[O:17])=[CH:11][C:10]=2[F:32])[CH:6]=[CH:5][N:4]=1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-(4-(3-chloro-2-(diphenylmethyleneamino)pyridin-4-yloxy)-3-fluorophenyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxamide (Preparation 1G, 127 mg, 0.2 mmol) in EtOH (5 mL) and THF (5 mL) at 0° C., was added NaBH4 (300 mg, 7.93 mmol). The mixture was stirred at 0° C. for 3 h, and then at rt overnight. The reaction was quenched with water, extracted with DCM, and dried over MgSO4. After filtration and concentration in vacuo, 120 mg of the desired material was obtained as a white solid. MS (ESI+) m/z 635 (M+H)+.

Workup

customat rt
customovernight
customThe reaction was quenched with water
extractionextracted with DCM
dry with materialdried over MgSO4
filtrationAfter filtration and concentration in vacuo

Sources & evidence

ORD record: ord-be18e2fa125a4d5ca4317ce16b9734a3
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258118B2

Reaction notes

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