Trifluoroacetic acid → HCID 57469113, compound

HRID 1928486Notes

Reaction equation

HRID 1928486 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]([C:27]4[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=4)[CH:24]=[C:23]([CH3:35])[N:22]=3)[N:16]=2)[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>>[C:33]([C:30]1[CH:29]=[CH:28][C:27]([C:25]2[CH:24]=[C:23]([CH3:35])[N:22]=[C:21]([C:17]3[N:16]=[C:15]([C:11]4[CH:10]=[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])[CH:14]=[CH:13][CH:12]=4)[CH:20]=[CH:19][CH:18]=3)[N:26]=2)=[CH:32][CH:31]=1)#[N:34]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57469112HCID 57469112, compound

Product 1

HCID 57469113HCID 57469113, compoundYield 67%

Conditions

Temperature
23 °C

Procedure

To N-tert-butyl-3-{6-[4-(4-cyano-phenyl)-6-methyl-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonamide (Example 441) (0.080 g, 0.165 mmol) was added TFA (2 mL) and the reaction mixture was stirred at 23° C. for 3 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 light brown solid (0.047 g, 67%). MS (ISP) 428.1 [(M+H)+]; mp 255° 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-8e20d97a9579426bae180b8b6fcc0e77
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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