2,3-Difluoroaniline → 2-(2,3-Difluorophenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amide

HRID 1868391Notes

Reaction equation

HRID 1868391 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.[F:22][C:23]1[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25]>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:25][C:24]3[CH:26]=[CH:27][CH:28]=[C:29]([F:30])[C:23]=3[F:22])=[N:15][CH:16]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 782782,3-DifluoroanilineHCID 57982581HCID 57982581, compound

Product 1

HCID 579826092-(2,3-Difluorophenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amideYield 24.8%

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 2,3-difluoroaniline (Aldrich) (113 mg) and the mixture was stirred at reflux for 47 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 a mass directed auto-preparative system to give the title compound (16 mg)

Workup

  1. temperatureat reflux for 47 hours
  2. customThe dioxan was removed
  3. custompurified

Sources & evidence

ORD record
ord-558ba206898b467781d8edca74362675
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

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