Methanol → HCID 86597676, compound

HRID 1951676Notes

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-4466c6b516304254bbfbd266decc8794
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404708B2

Reaction notes

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