Trifluoroacetic acid → HCID 68693554, compound

HRID 1928367Notes

Reaction equation

HRID 1928367 reaction equation
C(OC([NH:8][S:9]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[N:24]=[C:23]([C:25]3[CH:30]=[C:29]([C:31]4[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=4)[CH:28]=[C:27]([CH3:41])[N:26]=3)[CH:22]=[CH:21][N:20]=2)[CH:14]=1)(=[O:11])=[O:10])=O)(C)(C)C.C(O)(C(F)(F)F)=O>>[CH3:41][C:27]1[N:26]=[C:25]([C:23]2[CH:22]=[CH:21][N:20]=[C:19]([C:15]3[CH:14]=[C:13]([NH:12][S:9]([NH2:8])(=[O:11])=[O:10])[CH:18]=[CH:17][CH:16]=3)[N:24]=2)[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:39])([F:38])[F:40])=[CH:33][CH:32]=2)[CH:28]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68695466HCID 68695466, compound

Product 1

HCID 68693554HCID 68693554, compoundYield 78.3%

Conditions

Temperature
23 °C

Procedure

To N-(tert-butoxycarbonyl)-N′-(3-{4-[6-methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-pyrimidin-2-yl}-phenyl)-sulfamide (example 335) (0.100 g, 0.171 mmol) was added TFA (5 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 a white solid (0.065 g, 78%). MS (ISP) 486.3 [(M+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-0820f359342149a9b4af2c6bc3fc8429
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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