Trifluoroacetic acid → HCID 57469017, compound

HRID 1928298Notes

Reaction equation

HRID 1928298 reaction equation
C([NH:5][S:6]([C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)[CH:24]=[C:23]([CH2:37][CH3:38])[N:22]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH2:37]([C:23]1[N:22]=[C:21]([C:17]2[CH:16]=[C:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([S:6]([NH2:5])(=[O:8])=[O:7])[CH:10]=3)[CH:20]=[CH:19][CH:18]=2)[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:35])([F:36])[F:34])=[CH:29][CH:28]=2)[CH:24]=1)[CH3:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60209464HCID 60209464, compound

Product 1

HCID 57469017HCID 57469017, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of 3′-[6-ethyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-biphenyl-3-sulfonic acid tert-butylamide (example 265) (0.40 g, 0.742 mmol) in dichloromethane (10 mL) was added TFA (10 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), 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/diethyl ether and dried to yield the title compound as a white solid (0.022 g, 12%). MS (ISP) 481.2 [(M+H)+].

Workup

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness and saturated NaHCO3 solution (5 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/diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-12109ec6614c49ae9c30d5f1c28604b2
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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