Trifluoroacetic acid → 5-{3-[4-(3,4-Dichloro-phenyl)-6-methyl-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amide

HRID 1989482Notes

Reaction equation

HRID 1989482 reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[N:25]=[C:24]([CH3:26])[CH:23]=[C:22]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=4)[N:21]=3)[CH:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:34][C:29]1[CH:28]=[C:27]([C:22]2[CH:23]=[C:24]([CH3:26])[N:25]=[C:20]([C:16]3[CH:15]=[C:14]([C:11]4[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:13][CH:12]=4)[CH:19]=[CH:18][CH:17]=3)[N:21]=2)[CH:32]=[CH:31][C:30]=1[Cl:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57468949N-tert-Butyl-5-{3-[6-(3,4-dichloro-phenyl)-4-methyl-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amide

Product 1

HCID 574689485-{3-[4-(3,4-Dichloro-phenyl)-6-methyl-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amideYield 15.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of N-tert-butyl-5-{3-[6-(3,4-dichloro-phenyl)-4-methyl-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amide (0.39 g) in dichloromethane (6 mL) was added TFA (6 mL) and the reaction mixture was allowed to stir at room temperature for 15 h. The mixture was evaporated to dryness and saturated NaHCO3 solution (4 mL), diethyl ether and heptane were added. The mixture was stirred at room temperature for 1 h, the precipitate was collected by filtration and further purified by flash chromatography (heptane/ethyl acetate) and crystallization (dichloromethane/heptane) to yield the title compound as a light brown solid (0.054 g, 11%). MS (ISP) 476.0 [(M+H)+]; mp 238° C.

Workup

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness and saturated NaHCO3 solution (4 mL), diethyl ether and heptane
  3. additionwere added
  4. stirringThe mixture was stirred at room temperature for 1 h
  5. filtrationthe precipitate was collected by filtration
  6. customfurther purified by flash chromatography (heptane/ethyl acetate) and crystallization (dichloromethane/heptane)

Sources & evidence

ORD record
ord-dee645100e8f4dca95cb87263e47eb71
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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