Trifluoroacetic acid → HCID 57468987, compound

HRID 1989519Notes

Reaction equation

HRID 1989519 reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[N:15]=[CH:16][N:17]([C:19]3[N:24]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=4)[CH:22]=[C:21]([CH3:33])[N:20]=3)[CH:18]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:32][C:27]1[CH:26]=[C:25]([C:23]2[CH:22]=[C:21]([CH3:33])[N:20]=[C:19]([N:17]3[CH:18]=[C:14]([C:11]4[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:13][CH:12]=4)[N:15]=[CH:16]3)[N:24]=2)[CH:30]=[CH:29][C:28]=1[Cl:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 602094485-{1-[4-(3,4-dichloro-phenyl)-6-methyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiophene-2-sulfonic acid tert-butyl amide

Product 1

HCID 57468987HCID 57468987, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of 5-{1-[4-(3,4-dichloro-phenyl)-6-methyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiophene-2-sulfonic acid tert-butyl amide (0.41 g) in dichloromethane (5 mL) was added TFA (5 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 (10 mL) was added. The mixture was stirred at room temperature for 30 min, the precipitate was collected by filtration and washed with water. The crude product was further purified by crystallization (MeOH/diethyl ether) to yield the title compound as a light brown solid (0.28 g, 79%). MS (ISP) 466.1 [(M+H)+]; mp 253.5° C.

Workup

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness and saturated NaHCO3 solution (10 mL)
  3. additionwas added
  4. stirringThe mixture was stirred at room temperature for 30 min
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water
  7. customThe crude product was further purified by crystallization (MeOH/diethyl ether)

Sources & evidence

ORD record
ord-c4df68b6c9c64abe9c9000f2d3992a12
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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