N,N'-Dimethylethylenediamine → HCID 16063723, compound

HRID 421256Notes

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[CH:42]2[C:43](=[O:47])[NH:44][CH2:45][CH2:46][N:41]2[CH2:40][CH2:39][O:38]1.CNCCNC.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu](I)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:44]3[CH2:45][CH2:46][N:41]4[CH:42]([CH2:37][O:38][CH2:39][CH2:40]4)[C:43]3=[O:47])=[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 150 mg (0.281 mmol) of 2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-chloro-4-(4-fluoro-2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide (WO 2005/002577), 120 mg (0.768 mmol) of hexahydropyrazino[2,1-c][1,4]oxazin-9(6H)-one (D7), 60 μL (0.563 mmol) of N,N′-dimethylethylenediamine, 110 mg (0.578 mmol) of copper iodide, 183 mg (0.562 mmol) of cesium carbonate; the reagents were dissolved in 4.5 ml of dioxane. The reaction mixture is stirred overnight at 150° C. The crude was purified by chromatography (silica, cyclohexane/EtOAc 90/10-30/70) affording the title compound as a white solid: 73 mg, 0.111 mmol, 40% yield.

Workup

customA 8 ml sealed vial
customThe crude was purified by chromatography (silica, cyclohexane/EtOAc 90/10-30/70)

Sources & evidence

ORD record: ord-b8aa52d9187b44f0a8c604c3a2a5b85b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097618B2

Reaction notes

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