Trifluoroacetic acid → 3-(6'-Methyl-6''-trifluoromethyl-[2,2';4',3'']terpyridin-6-yl)-benzenesulfonamide

HRID 1962943Notes

Reaction equation

HRID 1962943 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: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:18]=[CH:17][CH:16]=2)[CH:10]=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:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:11]3[CH:10]=[C:9]([S:6]([NH2:5])(=[O:8])=[O:7])[CH:14]=[CH:13][CH:12]=3)[N:20]=2)[CH:26]=[C:25]([C:27]2[CH:28]=[N:29][C:30]([C:33]([F:35])([F:34])[F:36])=[CH:31][CH:32]=2)[CH:24]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67392744HCID 67392744, compound

Product 1

HCID 673939233-(6'-Methyl-6''-trifluoromethyl-[2,2';4',3'']terpyridin-6-yl)-benzenesulfonamideYield 48%

Conditions

Temperature
23 °C

Procedure

To N-tert-butyl-3-(6′-methyl-6″-trifluoromethyl-[2,2′;4′,3″]terpyridin-6-yl)-benzenesulfonamide (Example 29) (0.075 g, 0.142 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 an off-white solid (0.032 g, 48%). MS (ISP) 471.0 [(M+H)+]; mp 233-234° 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-d27d70f950254e18913a093233edfc02
Source dataset
uspto-grants-2013_04
Patent number
US08415380B2

Reaction notes

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