Potassium Carbonate → HCID 16063687, compound

HRID 2245471Notes

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[CH2:43][NH:42][CH2:41][CH2:40][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[CH2:43][CH2:37][C@@H:38]4[CH2:46][CH2:45][CH2:44][N:39]4[CH2:40][CH2:41]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

A 8 ml sealed vial was charged with 60 mg (0.112 mmoles) of 2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-chloro-4-(4-fluoro-2-methylphenyl) -3-pyridinyl]-N,2-dimethylpropanamide (WO 2005/002577), 47 mg (0.335 mmol) of (9aS) -octahydro-1H -pyrrolo[1,2-d][1,4]diazepine (D6), 31 mg of potassium carbonate (0.224 mmol); the reagents were dissolved in 0.5 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 from cyclohexane/ethyl acetate 1:1, to ethyl acetate 100% and affording 32 mg of the title compound as pale yellow solid.

Workup

customA 8 ml sealed vial
extractionback extracted with DCM
customthe crude material was purified on SPE cartridge (Silica)
washeluting with a gradient from cyclohexane/ethyl acetate 1:1, to ethyl acetate 100%

Sources & evidence

ORD record: ord-bdbfe00665b74a7fb4679d9673cf9318
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683056B2

Reaction notes

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