3-Chloro-4-fluoroaniline → 2-(3 Chloro-4-fluorophenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amide

HRID 1868379Notes

Reaction equation

HRID 1868379 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.[Cl:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[F:30])[NH2:26]>O1CCOCC1>[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:26][C:25]3[CH:27]=[CH:28][C:29]([F:30])=[C:23]([Cl:22])[CH:24]=3)=[N:15][CH:16]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 579825812-Chloro-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amide

Product 1

HCID 103880012-(3 Chloro-4-fluorophenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amideYield 79.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-chloro-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amide (100 mg) in 1,4-dioxan (1 ml) was added 3-chloro-4-fluoroaniline (228 mg, ex Lancaster) and the solution stirred at reflux for 4 hours. Dioxan 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 triturated with isohexane to afford the title compound (107 mg).

Workup

  1. temperatureat reflux for 4 hours
  2. customDioxan was removed under reduced pressure and ethyl acetate (5 ml)
  3. additionadded
  4. washThe solution was washed sequentially with 2N hydrochloric acid (2×3 ml) and water (3×3 ml), dried MgSO4),
  5. customevaporated
  6. customtriturated with isohexane

Sources & evidence

ORD record
ord-a3e93f0f2ac34d74adc4c84e53c5b44f
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

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