2-Chloro-p-toluidine → 2-(2-Chloro-4-methylphenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amide

HRID 1868393Notes

Reaction equation

HRID 1868393 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:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=1[NH2:30]>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:30][C:24]3[CH:25]=[CH:26][C:27]([CH3:29])=[CH:28][C:23]=3[Cl:22])=[N:15][CH:16]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 120072-Chloro-p-toluidineHCID 579825812-Chloro-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amide

Product 1

HCID 579826322-(2-Chloro-4-methylphenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-chloro-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amide (Example 166a) (50 mg) in 1,4-dioxan (1 ml) was added 2-chloro-4-methylphenylamine (Aldrich) (109 mg) the mixture was stirred at reflux for 24 hours using a Radleys Greenhouse Parallel Synthesiser. The dioxan was removed using a nitrogen blow down unit The residue was taken up into methanol (0.5 ml) and dimethylsulfoxide (0.5 ml) and purified using mass directed auto-preparative system to give the title compound) (24 mg)

Workup

  1. temperatureat reflux for 24 hours
  2. customThe dioxan was removed
  3. custompurified

Sources & evidence

ORD record
ord-1f21c8b5706f4bda825d89daaabdde18
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

Loading…