Trifluoroacetic acid → HCID 69076481, compound

HRID 1928339Notes

Reaction equation

HRID 1928339 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:16]=[CH:17][N:18]([C:20]3[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)[N:21]=3)[CH:19]=2)[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([C:22]2[N:21]=[C:20]([N:18]3[CH:19]=[C:15]([C:11]4[CH:10]=[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])[CH:14]=[CH:13][CH:12]=4)[NH:16][CH2:17]3)[CH:25]=[C:24]([CH3:26])[CH:23]=2)=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57469036HCID 57469036, compound

Product 1

HCID 69076481HCID 69076481, compoundYield 101%

Conditions

Temperature
23 °C

Procedure

To N-tert-butyl-3-{1-[6-(4-chloro-phenyl)-4-methyl-pyridin-2-yl]-1H-imidazol-4-yl}-benzenesulfonamide (example 298) (0.028 g, 0.058 mmol) was added TFA (2 mL) and the reaction mixture was stirred at 23° C. for 16 h. The mixture was evaporated to dryness and partitioned between EtOAc and saturated NaHCO3 solution, the organic layer was dried over Na2SO4. Removal of the solvent in vacuum left a crude product which was triturated with diethyl ether to give the title compound as an off-white solid (0.025 g, 101%). MS (ISP) 425.1 [(M+H)+] and 427 [(M+2+H)+].

Workup

  1. customThe mixture was evaporated to dryness
  2. custompartitioned between EtOAc and saturated NaHCO3 solution
  3. dry with materialthe organic layer was dried over Na2SO4
  4. customRemoval of the solvent in vacuum
  5. waitleft a crude product which
  6. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-fd23bab9b351403691941c42275c9f2c
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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