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

HRID 2074936Notes

Reaction equation

HRID 2074936 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:33])([CH3:32])[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][CH:27]=[CH:26][C:25]=2[CH3:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:36]1[CH:41]2[CH2:42][NH:43][CH2:44][CH2:45][N:40]2[CH2:39][CH2:38][O:37]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.ClCCl>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:33])([CH3:32])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:43]3[CH2:44][CH2:45][N:40]4[CH:41]([CH2:36][O:37][CH2:38][CH2:39]4)[CH2:42]3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 102295322-(3,5-bis(trifluoromethyl)phenyl)-N-(6-chloro-4-(o-tolyl)pyridin-3-yl)-N,2-dimethylpropanamideHCID 19777228Octahydropiperazino[2,1-c]morpholine

Product 1

HCID 160636152-[3,5-bis(trifluoromethyl)phenyl]-N-[6-(hexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl)-4-(2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamideYield 38.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-chloro-4-(2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide [WO 2002/16324A1] (200 mg, 0.388 mmol), octahydropyrazino[2,1-c][1,4]oxazine (EP472826, 111 mg, 0.776 mmol), and potassium carbonate (161 mg, 1.165 mmol) in 1 mL of DMSO was heated to 150° C. for 47 h. It was worked up by diluting with dichloromethane and extracting with brine. The organics were dried (Na2SO4), and the solvent removed. The product was purified by flash chromatography: silica, dichloromethane to dichloromethane: MeOH 95:5. Obtained 92 mg of the title compound.

Workup

  1. extractionextracting with brine
  2. dry with materialThe organics were dried (Na2SO4)
  3. customthe solvent removed
  4. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-135686041900402886068895f7d7f9dd
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

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