Potassium Carbonate → HCID 16063686, compound

HRID 2074901Notes

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.[CH2:37]1[NH:42][CH2:41][C:40](=[O:43])[N:39]2[CH2:44][CH2:45][CH2:46][C@@H:38]12.C(=O)([O-])[O-].[K+].[K+].[NH4+].[Cl-]>CS(C)=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[CH:19]=[N:20][C:21]([N:42]3[CH2:41][C:40](=[O:43])[N:39]4[CH2:44][CH2:45][CH2:46][C@@H:38]4[CH2:37]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: 150 °C

Procedure

The title compound was prepared starting from 135 mg (0.253 mmoles) of 2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-chloro-4-(4-fluoro-2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide (WO 2005/002577), 70 mg (0.5 mmol) of (8aS)-hexahydropyrrolo[1,2-a]pyrazin-4(1H)-one (EP 300189), 70 mg (0.5 mmol) of potassium carbonate; the reagents were dissolved in 0.8 ml of DMSO. The reaction mixture was heated at 150° C. overnight and then added to a saturated NH4Cl solution and back extracted with DCM; the crude material was purified on SPE cartridge (Silica) eluting with a gradient cyclohexane/ethyl acetate 9:1, to ethyl acetate 100% and affording 24 mg of the title compound as pale yellow solid.

Workup

customThe title compound was prepared
extractionback extracted with DCM
customthe crude material was purified on SPE cartridge (Silica)
washeluting with a gradient cyclohexane/ethyl acetate 9:1, to ethyl acetate 100%

Sources & evidence

ORD record: ord-5036ba8bcef0407bb9c7b79f889a7974
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919491B2

Reaction notes

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