Trifluoroacetic acid → 3-(4-{4-[3-(2,2,2-Trifluoro-ethoxy)-4-trifluoromethyl-phenyl]-6-trifluoromethyl-pyrimidin-2-yl}-pyridin-2-yl)-benzenesulfonamide

HRID 1928494Notes

Reaction equation

HRID 1928494 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:20]=[C:19]([C:21]3[N:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[C:29]([O:37][CH2:38][C:39]([F:42])([F:41])[F:40])[CH:28]=4)[CH:24]=[C:23]([C:43]([F:46])([F:45])[F:44])[N:22]=3)[CH:18]=[CH:17][N:16]=2)[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[F:42][C:39]([F:40])([F:41])[CH2:38][O:37][C:29]1[CH:28]=[C:27]([C:25]2[CH:24]=[C:23]([C:43]([F:45])([F:46])[F:44])[N:22]=[C:21]([C:19]3[CH:18]=[CH:17][N:16]=[C:15]([C:11]4[CH:10]=[C:9]([S:6]([NH2:5])(=[O:8])=[O:7])[CH:14]=[CH:13][CH:12]=4)[CH:20]=3)[N:26]=2)[CH:32]=[CH:31][C:30]=1[C:33]([F:34])([F:36])[F:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60209495HCID 60209495, compound

Product 1

HCID 602094943-(4-{4-[3-(2,2,2-Trifluoro-ethoxy)-4-trifluoromethyl-phenyl]-6-trifluoromethyl-pyrimidin-2-yl}-pyridin-2-yl)-benzenesulfonamideYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled and stirred solution of 3-(4-{4-[3-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-phenyl]-6-trifluoromethyl-pyrimidin-2-yl}-pyridin-2-yl)-benzenesulfonic acid tert-butylamide (0.21 g) in dichloromethane (5 ml) was added TFA (5 ml) and the reaction mixture was allowed to stir at room temperature for 15 h. The mixture was evaporated to dryness, poured into saturated NaHCO3 solution (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4) and evaporated. Further purification by crystallization (diethyl ether) yielded the title compound as an off-white solid (0.15 g, 77%). MS (ISP) 623.2 [(M+H)+]; mp 211° C.

Workup

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness
  3. additionpoured into saturated NaHCO3 solution (20 ml)
  4. extractionextracted with ethyl acetate (2×30 ml)
  5. washThe combined organic layers were washed with brine (20 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customFurther purification
  9. customby crystallization (diethyl ether)

Sources & evidence

ORD record
ord-fa98e2600eaa4e25ab9dff9d06d5a546
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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