Trifluoroacetic acid → 5-[6'-Methyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-thiophene-2-sulfonic acid amide

HRID 1928345Notes

Reaction equation

HRID 1928345 reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=4)[CH:23]=[C:22]([CH3:36])[N:21]=3)[CH:17]=[CH:16][CH:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>>[CH3:36][C:22]1[N:21]=[C:20]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([C:11]3[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:13][CH:12]=3)[N:19]=2)[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:34])([F:33])[F:35])=[CH:28][CH:27]=2)[CH:23]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 247609715-[6'-Methyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-thiophene-2-sulfonic acid tert-butylamide

Product 1

HCID 247598715-[6'-Methyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-thiophene-2-sulfonic acid amideYield 85.4%

Conditions

Temperature
23 °C

Procedure

To 5-[6′-methyl-4′-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl-6-yl]-thiophene-2-sulfonic acid tert-butylamide (example 305) (0.170 g, 0.32 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 TBME 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 (0.130 g, 85%). MS (ISP) 476.2 [(M+H)+]; mp 243° C. (dec.).

Workup

  1. customThe mixture was evaporated to dryness
  2. custompartitioned between TBME 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-74686ef4b0844d8f91c97bce26c2d0b8
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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