Trifluoroacetic acid → 3-[6'-Methyl-4'-(4-trifluoromethoxy-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamide

HRID 1928481Notes

Reaction equation

HRID 1928481 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:20]=[C:19]([C:21]3[CH:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=4)[CH:24]=[C:23]([CH3:38])[N:22]=3)[CH:18]=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>>[CH3:38][C:23]1[N:22]=[C:21]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:11]3[CH:10]=[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])[CH:14]=[CH:13][CH:12]=3)[N:20]=2)[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:35])[F:36])=[CH:29][CH:28]=2)[CH:24]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24760219N-tert-Butyl-3-[6'-methyl-4'-(4-trifluoromethoxy-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamide

Product 1

HCID 247602203-[6'-Methyl-4'-(4-trifluoromethoxy-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonamideYield 76%

Conditions

Temperature
23 °C

Procedure

To N-tert-butyl-3-{6-[4-methyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonamide (Example 436) (0.100 g, 0.185 mmol) was added TFA (3 mL) and the reaction mixture was stirred at 23° C. for 3 h. The mixture was partitioned between EtOAc and saturated NaHCO3 solution, the organic layer was dried over MgSO4. 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 (0.068 g, 76%). MS (ISP) 486.0 [(M+H)+]; mp 231° C. (dec.).

Workup

  1. customThe mixture was partitioned between EtOAc and saturated NaHCO3 solution
  2. dry with materialthe organic layer was dried over MgSO4
  3. customRemoval of the solvent in vacuum
  4. waitleft a crude product which
  5. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-1f4fca0ec3bb4dd9afdc6e3f3288b07f
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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