Methanol → HCID 86597676, compound

HRID 547768Notes

Reaction equation

[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([C:13]([CH3:39])([CH3:38])[C:14]([N:16]([C:18]2[C:19]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])=[CH:20][C:21]([N:24]3[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]3)=[N:22][CH:23]=2)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CO.C([BH3-])#[N:45].[Na+]>C(OCC)(=O)C>[NH2:45][CH:27]1[CH2:28][CH2:29][N:24]([C:21]2[CH:20]=[C:19]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])[C:18]([N:16]([CH3:17])[C:14](=[O:15])[C:13]([C:5]3[CH:4]=[C:3]([C:2]([F:40])([F:41])[F:1])[CH:8]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:6]=3)([CH3:39])[CH3:38])=[CH:23][N:22]=2)[CH2:25][CH2:26]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 752 mg (1.26 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4′-(2-chloro-phenyl)-4-oxo-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-yl]-N-methyl-isobutyramide in 7 ml methanol 970 mg (12.6 mmol) ammonium acetate were added at room temperature. The mixture was stirred 5 minutes at this temperature, cooled to 0° C. and treated with 119 mg (1.89 mmol) sodium cyanoborohydride. The reaction mixture was allowed to slowly warm to room temperature during 5 h, followed by dilution with 20 ml ethyl acetate, washing with 10 ml brine and extraction with 20 ml ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography to give 480 mg (64%) of the title compound as a white foam.

Workup

temperatureto slowly warm to room temperature during 5 h
washwashing with 10 ml brine and extraction with 20 ml ethyl acetate
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated in vacuo
custompurified by flash chromatography

Sources & evidence

ORD record: ord-d7e39c75c8104fc482f8684a469b3b94
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07939533B2

Reaction notes

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