Trifluoroacetic acid → 3'-(6'-Methyl-6-trifluoromethyl-[3,4']bipyridinyl-2'-yl)-biphenyl-3-sulfonic acid amide

HRID 906304Notes

Reaction equation

HRID 906304 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:28]=[N:29][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:32]=4)[CH:24]=[C:23]([CH3:37])[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>>[CH3:37][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:7])=[O:8])[CH:10]=3)[CH:20]=[CH:19][CH:18]=2)[CH:26]=[C:25]([C:27]2[CH:28]=[N:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=2)[CH:24]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 25097444HCID 25097444, compound

Product 1

HCID 250974453'-(6'-Methyl-6-trifluoromethyl-[3,4']bipyridinyl-2'-yl)-biphenyl-3-sulfonic acid amideYield 75%

Conditions

Temperature
23 °C

Procedure

To 3′-(6′-methyl-6-trifluoromethyl-[3,4′]bipyridinyl-2′-yl)-biphenyl-3-sulfonic acid tert-butylamide (Example 31) (0.150 g, 0.285 mmol) was added TFA (2 mL) and the reaction mixture was stirred at 23° C. for 16 h. The mixture was 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 (0.090 g, 75%). MS (ISP) 470.1 [(M+H)+]; mp 227-232° C.

Workup

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

Sources & evidence

ORD record
ord-af9939cc24944b8793b6225b96941e6e
Source dataset
uspto-grants-2011_09
Patent number
US08012986B2

Reaction notes

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