3-Aminobenzonitrile → 2-(3-Cyanophenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amide

HRID 1868380Notes

Reaction equation

HRID 1868380 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]([C:11]2[C:12]([C:18]([F:21])([F:20])[F:19])=[N:13][C:14](Cl)=[N:15][CH:16]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[C:26]#[N:27]>C(#N)C>[CH3:4][CH2:3][CH2:2][CH:1]([CH3:7])[CH3:6].[CH:1]1([CH2:7][NH:8][C:9]([C:11]2[C:12]([C:18]([F:21])([F:20])[F:19])=[N:13][C:14]([NH:22][C:23]3[CH:30]=[CH:29][CH:28]=[C:25]([C:26]#[N:27])[CH:24]=3)=[N:15][CH:16]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 167023-AminobenzonitrileHCID 579825812-Chloro-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amide

Product 2

HCID 78922-MethylpentaneHCID 103637952-(3-Cyanophenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amideYield 118%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
200 °C

Procedure

To a solution of 2-chloro-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amide (50 mg) in acetonitrile (0.5 ml) was added 3-aminobenzonitrile (92 mg, ex Aldrich) and the solution heated at 200° C. under microwave conditions for 45 minutes. Acetonitrile was removed under reduced pressure and ethyl acetate (5 ml) added. The solution was washed sequentially with 2N hydrochloric acid (2×3 ml) and water (3×3 ml), dried (MgSO4), evaporated and the residue purified using silica gel chromatography with 1:1 ethyl acetate:isohexane to afford the title compound (37 mg).

Workup

  1. customAcetonitrile was removed under reduced pressure and ethyl acetate (5 ml)
  2. additionadded
  3. washThe solution was washed sequentially with 2N hydrochloric acid (2×3 ml) and water (3×3 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customthe residue purified

Sources & evidence

ORD record
ord-bebd050383524bc49e5124d9fbbb0695
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

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