Potassium Carbonate → 2-[3,5-Bis(trifluoromethyl)phenyl]-N-[4-(4-fluoro-2-methylphenyl)-6-(hexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl)-3-pyridinyl]-N,2-dimethylpropanamide

HRID 2245473Notes

Reaction equation

HRID 2245473 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[CH2:43][NH:44][CH2:45][CH2:46][N:41]2[CH2:40][CH2:39][O:38]1.C(=O)([O-])[O-].[K+].[K+]>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:44]3[CH2:45][CH2:46][N:41]4[CH:42]([CH2:37][O:38][CH2:39][CH2:40]4)[CH2:43]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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19777228Octahydropiperazino[2,1-c]morpholineHCID 235027842-(3,5-Bis(trifluoromethyl)phenyl)-N-(6-chloro-4-(4-fluoro-2-methylphenyl)pyrid-3-yl)-N,2-dimethylpropanamide

Product 1

HCID 160637262-[3,5-Bis(trifluoromethyl)phenyl]-N-[4-(4-fluoro-2-methylphenyl)-6-(hexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl)-3-pyridinyl]-N,2-dimethylpropanamideYield 57.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 8 ml sealed vial was charged with 124 mg (0.233 mmol) of 2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-chloro-4-(4-fluoro-2-methylphenyl) -3-pyridinyl]-N,2-dimethylpropanamide (WO 2005/002577); 83 mg (0.584 mmol) of octahydropyrazino[2,1-c][1,4]oxazine (EP 472826), 90 mg (0.701 mmol) of potassium carbonate; the reagents were dissolved in 0.5 ml of DMSO. The crude product was purified by flash chromatography (silica, cyclohexane/EtOAc 90/10-30/70) affording the title compound as a white solid 85 mg (0.133 mmol).

Workup

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

Sources & evidence

ORD record
ord-b12248193bde44acb8b450c45b55073f
Source dataset
uspto-grants-2010_03
Patent number
US07683056B2

Reaction notes

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