Dichloromethane → HCID 86642508, compound

HRID 421281Notes

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.[C:37]1(=O)[NH:42][CH2:41][CH2:40][N:39]2[CH2:43][CH2:44][CH2:45][C@@H:38]12.CNCCNC.ClCCl.[O:56]1CCOC[CH2:57]1>[Cu]I>[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][N:39]4[CH2:43][CH2:44][CH2:45][C@H:38]4[C@@H:37]3[CH2:57][OH:56])=[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: 120 °C

Procedure

A suspension of 2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-chloro-4-(4-fluoro-2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide [WO 2005/002577] (100 mg), (8aS)-hexahydropyrrolo[1,2-a]pyrazin-1(2H)-one (D76, 79 mg, 3 eq), CuI (72 mg, 2 eq), N,N′-Dimethylethylenediamine (40 μl, 2 eq) and CsCO3(122.4 mg, 2 eq) in dioxane (3 ml) was heated in a sealed tube at 80° C. for 4 hrs and at 120° C. overnight. The reaction mixture was taken up with dichloromethane and it was washed with NH4Cl aq. The organic phase was evaporated to dryness and the crude was purified by chromatography (silica cartridge, cyclohexane:EtOAc 1:1 to 0:1) to give the title compound (39 mg).

Workup

washwas washed with NH4Cl aq. The organic phase
customwas evaporated to dryness
customthe crude was purified by chromatography (silica cartridge, cyclohexane:EtOAc 1:1 to 0:1)

Sources & evidence

ORD record: ord-a7082072f98a470ba1cfb11a7cfca557
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097618B2

Reaction notes

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