Potassium Carbonate → HCID 86597694, compound

HRID 1951714Notes

Reaction equation

[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C:13]([CH3:34])([CH3:33])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21](Cl)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH:37][CH2:38][CH:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.[Cl-].[Li+].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C:13]([CH3:34])([CH3:33])[C:14]([N:16]([C:18]2[C:23]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[CH3:31])=[CH:22][C:21]([N:42]3[CH2:43][CH2:44][CH:39]([CH2:38][OH:37])[CH2:40][CH2:41]3)=[N:20][CH:19]=2)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 0.50 g (0.94 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-chloro-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide, 0.32 g (2.8 mmol) 4-(hydroxymethyl)piperidine, 0.12 g (2.8 mmol) lithium chloride and 0.39 g (2.8 mmol) potassium carbonate in 5 ml DMSO was heated at 140° C. for 24 h. After cooling to room temperature the reaction mixture was diluted with water and extracted with three portions of dichloromethane. The combined organic extracts were dried over sodium sulphate and concentrated. Flash column chromatography gave 0.42 g (74%) of the title compound as a white solid.

Workup

temperatureAfter cooling to room temperature the reaction mixture
extractionextracted with three portions of dichloromethane
dry with materialThe combined organic extracts were dried over sodium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-b7c74d9a13694f2e8be296838c11a9a2
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404708B2

Reaction notes

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