Potassium Carbonate → HCID 86597712, compound

HRID 547829Notes

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.[CH3:37][C@@H:38]1[CH2:43][NH:42][CH2:41][CH2:40][NH:39]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[OH-].[Na+]>[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]([N:42]3[CH2:41][CH2:40][NH:39][C@H:38]([CH3:37])[CH2:43]3)=[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

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 0.20 g (0.38 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-chloro-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide, 0.11 g (1.1 mmol) (R)-2-methylpiperazine and 0.10 g (0.72 mmol) potassium carbonate in 0.3 ml dimethyl sulfoxide was heated at 180° C. under microwave irradiation in a sealed tube for 30 min. After cooling to room temperature the reaction mixture was diluted with a 0.3 M aqueous solution of sodium hydroxide and extracted with three portions of tert-butyl methyl ether. The combined organic extracts were dried over sodium sulfate and concentrated. Flash column chromatography gave 0.12 g (51%) of the title compound as an off-white solid.

Workup

temperatureAfter cooling to room temperature the reaction mixture
extractionextracted with three portions of tert-butyl methyl ether
dry with materialThe combined organic extracts were dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-cb87bfa707634b439d6291481e331987
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07939533B2

Reaction notes

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