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

HRID 1928406Notes

Reaction equation

HRID 1928406 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]([CH3:34])[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:33][C:30]1[CH:31]=[CH:32][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:7])=[O:8])=[CH:13][CH:12]=4)[CH:19]=[CH:18][CH:17]=3)[N:21]=2)=[CH:28][C:29]=1[CH3:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57469056N-tert-Butyl-5-{3-[6-(4-chloro-3-methyl-phenyl)-4-methyl-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amide

Product 1

HCID 574690555-{3-[4-(4-Chloro-3-methyl-phenyl)-6-methyl-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amideYield 25.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of N-tert-butyl-5-{3-[6-(4-chloro-3-methyl-phenyl)-4-methyl-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amide (0.405 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 (5 ml), diethylether 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 (diethyl ether/heptane) to yield the title compound as an off-white solid (0.093 g, 20%). MS (ISP) 456.1 [(M+H)+]; mp 240° C.

Workup

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness and saturated NaHCO3 solution (5 ml), diethylether 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 (diethyl ether/heptane)

Sources & evidence

ORD record
ord-601ad91427dd4ff8bb07a33fa6a30025
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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