Trifluoroacetic acid → HCID 25098002, compound

HRID 906299Notes

Reaction equation

HRID 906299 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[N:26]=[C:25]([CH3:27])[CH:24]=[C:23]([C:28]4[CH:29]=[N:30][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:33]=4)[N:22]=3)[N:16]=2)[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>>[CH3:27][C:25]1[CH:24]=[C:23]([C:28]2[CH:29]=[N:30][C:31]([C:34]([F:36])([F:37])[F:35])=[CH:32][CH:33]=2)[N:22]=[C:21]([C:17]2[N: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)[CH:20]=[CH:19][CH:18]=2)[N:26]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 25098000HCID 25098000, compound

Product 1

HCID 25098002HCID 25098002, compoundYield 98%

Conditions

Temperature
23 °C

Procedure

To N-tert-butyl-3-{6-[4-methyl-6-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonamide (Example 26) (0.092 g, 0.174 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 (0.080 g, 98%). MS (ISP) 472.0 [(M+H)+]; mp 254° 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-def74b4ab5204a68aeebb750161cd9d2
Source dataset
uspto-grants-2011_09
Patent number
US08012986B2

Reaction notes

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