Trifluoroacetic acid → HCID 57468911, compound

HRID 1989442Notes

Reaction equation

HRID 1989442 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]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)[CH:23]=[C:22]([C:33]([F:36])([F:35])[F:34])[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:32][C:29]1[CH:28]=[CH:27][C:26]([C:24]2[CH:23]=[C:22]([C:33]([F:35])([F:36])[F:34])[N:21]=[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:25]=2)=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60209427HCID 60209427, compound

Product 1

HCID 57468911HCID 57468911, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of 5-{3-[4-(4-chloro-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid tert-butylamide (example 169) (0.175 g, 0.32 mmol) in dichloromethane (4 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 (4 mL), diethyl ether and heptane were added. The mixture was stirred at room temperature for 1 h, the precipitate was collected by filtration, washed with water and heptane and dried to yield the title compound as a white solid (0.12 g, 75%). MS (ISN) 494.1 [(M−H)−]; mp 226° 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. washwashed with water and heptane
  7. customdried

Sources & evidence

ORD record
ord-c2358c0d7a6d409ba8c2e2510783da20
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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