3-Chloro-4-fluoroaniline → 2-(3-Chloro-4-fluoro-phenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclopentylmethyl-amide

HRID 1868396Notes

Reaction equation

HRID 1868396 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[C:11]([C:17]([F:20])([F:19])[F:18])=[N:12][C:13](Cl)=[N:14][CH:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[F:29])[NH2:25]>O1CCOCC1>[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[C:11]([C:17]([F:20])([F:19])[F:18])=[N:12][C:13]([NH:25][C:24]3[CH:26]=[CH:27][C:28]([F:29])=[C:22]([Cl:21])[CH:23]=3)=[N:14][CH:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 579826072-Chloro trifluoromethyl-pyrimidin-5-carboxylic acid (cyclopentylmethyl)-amide

Product 1

HCID 579826572-(3-Chloro-4-fluoro-phenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclopentylmethyl-amideYield 66.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclopentylmethyl-amide (116 mg Example 183a), 3-chloro-4-fluoroaniline (ex-Aldrich, 275 mg), and 1,4-dioxan (1.2 ml) were stirred at 100° C. under nitrogen for 6 h. The cooled reaction mixture was evaporated in vacuo, treated with ethyl acetate (5 ml), washed with aqueous 2M hydrochloric acid (2×3 ml), followed by brine, and dried (Na2SO4). The solution was evaporated in vacuo to give the title compound (104 mg).

Workup

  1. customThe cooled reaction mixture
  2. customwas evaporated in vacuo
  3. additiontreated with ethyl acetate (5 ml)
  4. washwashed with aqueous 2M hydrochloric acid (2×3 ml)
  5. dry with materialdried (Na2SO4)
  6. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-6125b9db4d6e40b2afbb0076039fa75a
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

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