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

HRID 1868397Notes

Reaction equation

HRID 1868397 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:28]=[CH:27][C:26]([F:29])=[CH:25][C:23]=1[NH2:24]>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:24][C:23]3[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:22]=3[Cl:21])=[N:14][CH:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 27365092-Chloro-5-fluoroanilineHCID 579826072-Chloro trifluoromethyl-pyrimidin-5-carboxylic acid (cyclopentylmethyl)-amide

Product 1

HCID 579826602-(2-Chloro-5-fluoro-phenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclopentylmethyl-amideYield 25.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-4-trifluoromethyl-pyrimidine-5-carboxylic acid cyclopentylmethyl-amide (100 mg Example 183a), 2-chloro-5-fluoroaniline (ex-Fluorochem, 237 mg), and 1,4-dioxan (1 ml) were stirred at 100° C. under nitrogen for 18 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 water (2×3 ml), and dried (Na2SO4). The solution was evaporated in vacuo and the residue purified by mass directed auto-preparative purification to give the title compound (35 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
  7. customthe residue purified by mass
  8. custompurification

Sources & evidence

ORD record
ord-4079c3b4f9ed4a2092ff0e35df278497
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

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