Potassium Carbonate → 1-[3,5-Bis(trifluoromethyl)phenyl]-N-{4-(4-fluoro-2-methylphenyl)-6-[(8aS)-6-oxohexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-3-pyridinyl}-N-methylcyclopropanecarboxamide

HRID 421249

Reaction equation

HRID 421249 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]2([C:16]([NH:18][C:19]3[CH:20]=[N:21][C:22](Cl)=[CH:23][C:24]=3[C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[CH3:32])=[O:17])[CH2:15][CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:36]1[NH:41][CH2:40][CH2:39][N:38]2[C:42](=[O:45])[CH2:43][CH2:44][C@@H:37]12.[C:46](=O)([O-])[O-].[K+].[K+].[NH4+].[Cl-]>CS(C)=O>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]2([C:16]([N:18]([C:19]3[CH:20]=[N:21][C:22]([N:41]4[CH2:40][CH2:39][N:38]5[C:42](=[O:45])[CH2:43][CH2:44][C@H:37]5[CH2:36]4)=[CH:23][C:24]=3[C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[CH3:32])[CH3:46])=[O:17])[CH2:15][CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 18439805(S)-Hexahydropyrrolo[1,2-A]pyrazin-6(2H)-oneHCID 592157801-[3,5-Bis(trifluoromethyl)phenyl]-N-[6-chloro-4-(4-fluoro-2-methylphenyl)-3-pyridinyl]cyclopropanecarboxamide

Product 1

HCID 160636491-[3,5-Bis(trifluoromethyl)phenyl]-N-{4-(4-fluoro-2-methylphenyl)-6-[(8aS)-6-oxohexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-3-pyridinyl}-N-methylcyclopropanecarboxamideYield 43.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

The title compound was prepared starting from 50 mg (0.094 mmoles) of 1-[3,5-bis(trifluoromethyl)phenyl]-N-[6-chloro-4-(4-fluoro-2-methylphenyl)-3-pyridinyl]cyclopropanecarboxamide (D2), 39 mg (0.278 mmol) of (8aS)-hexahydropyrrolo[1,2-a]pyrazin-6(2H)-one (WO 2003/066635), 26.2 mg (0.189 mmol) of potassium carbonate; the reagents were dissolved in 0.4 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 26 mg of the title compound as pale yellow solid.

Workup

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

Sources & evidence

ORD record
ord-68983ab4d6aa4821bbee3afaefdf4e83
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Linked notes

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