Dimethylformamide → 2-(3,5-Bis-trifluoromethyl-phenyl)-N-methyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-acetamide

HRID 379391Notes

Reaction equation

HRID 379391 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH2:13][C:14](O)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N1[CH:30]=[CH:29]N=C1)(N1C=CN=C1)=O.C[NH:32][C:33]1[C:34]([C:39]2[CH:44]=[C:43]([N:45]3[CH2:50][CH2:49][O:48][CH2:47][CH2:46]3)[C:42]([CH3:51])=[CH:41][CH:40]=2)=[N:35][CH:36]=CC=1.[CH3:52]N(C)C=O>>[F:10][C:9]([F:12])([F:11])[C:7]1[CH:6]=[C:5]([CH2:13][C:14]([N:35]([CH3:36])[C:34]2[CH:33]=[N:32][C:43]([N:45]3[CH2:46][CH2:47][O:48][CH2:49][CH2:50]3)=[CH:44][C:39]=2[C:40]2[CH:41]=[CH:42][CH:51]=[CH:52][C:29]=2[CH3:30])=[O:15])[CH:4]=[C:3]([C:2]([F:18])([F:1])[F:17])[CH:8]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 1235873,5-Bis(trifluoromethyl)phenylacetic acidHCID 69138572Methyl-(6-morpholin-4-yl-4-tolyl-pyridin-3-yl)-amine

Product 1

HCID 98501332-(3,5-Bis-trifluoromethyl-phenyl)-N-methyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-acetamideYield 94%

Procedure

To a solution of 300 mg (1.1 mmol) 3,5-bis(trifluoromethyl)-phenylacetic acid in 7 ml N,N-dimethylformamide were added 185 mg (1.14 mmol) 1,1′-carbonyl-diimidazole and the solution was stirred for 30 min at room temperature. After addition of 283 mg (1 mmol) of methyl-(6-morpholin-4-yl-4-tolyl-pyridin-3-yl)-amine (as described in step f) for the preparation of Example 23), the reaction mixture was heated over night at 90° C. After cooling to room temperature, the solvent was removed in vacuo and the residue was re-dissolved in 30 ml ethyl acetate. The organic phase was washed with water (2×30 ml), brine, dried (magnesium sulfate) and evaporated. Flash chromatography gave 506 mg (94%) of the title compound as a light brown foam.

Workup

  1. customfor the preparation of Example 23), the reaction mixture
  2. temperaturewas heated over night at 90° C
  3. temperatureAfter cooling to room temperature
  4. customthe solvent was removed in vacuo
  5. dissolutionthe residue was re-dissolved in 30 ml ethyl acetate
  6. washThe organic phase was washed with water (2×30 ml), brine
  7. dry with materialdried (magnesium sulfate)
  8. customevaporated

Sources & evidence

ORD record
ord-59883c904cfd4a8ca082ba37a00a81cf
Source dataset
uspto-grants-2001_10
Patent number
US06297375B1

Reaction notes

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