Trifluoroacetic acid → HCID 58054526, compound

HRID 1874698Notes

Reaction equation

HRID 1874698 reaction equation
CC([N:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][N:17]2[C:25]3[C:20](=[C:21]([CH:26]([F:28])[F:27])[CH:22]=[CH:23][CH:24]=3)[C:19]([N:29]([S:39]([C:42]3[S:43][C:44]([Cl:47])=[CH:45][CH:46]=3)(=[O:41])=[O:40])[S:30]([C:33]3[S:34][C:35]([Cl:38])=[CH:36][CH:37]=3)(=[O:32])=[O:31])=[N:18]2)[CH:11]=1)C(=O)[O-])(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:5][CH2:9][C:10]1[CH:11]=[C:12]([CH2:16][N:17]2[C:25]3[C:20](=[C:21]([CH:26]([F:27])[F:28])[CH:22]=[CH:23][CH:24]=3)[C:19]([N:29]([S:39]([C:42]3[S:43][C:44]([Cl:47])=[CH:45][CH:46]=3)(=[O:40])=[O:41])[S:30]([C:33]3[S:34][C:35]([Cl:38])=[CH:36][CH:37]=3)(=[O:32])=[O:31])=[N:18]2)[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86644813HCID 86644813, compound

Product 1

HCID 58054526HCID 58054526, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl[(3-{[3-{bis[(5-chloro-2-thienyl)sulfonyl]amino}-4-(difluoromethyl)-1H-indazol-1-yl]methyl}phenyl)methyl]carbamate (for a preparation see Intermediate 69) (60 mg, 0.079 mmol) was dissolved in dichloromethane (0.5 mL) and trifluoroacetic acid (0.125 mL) was added to the solution. and stirred for 1 h under nitrogen. The solution was concentrated under a stream of nitrogen and the off-white residue was dissolved in methanol and loaded onto a methanol conditioned sulphonic acid (SCX-2) cartridge (10 g). The cartridge was washed well with methanol, followed by 2M ammonia in methanol. Evaporation of the solvent from the ammoniacal fractions gave the title compound (26 mg, 54%) as a white solid. LCMS (System A) RT=1.11 min, ES+ve m/z 663/665 (M+H)+.

Workup

  1. concentrationThe solution was concentrated under a stream of nitrogen
  2. dissolutionthe off-white residue was dissolved in methanol
  3. washThe cartridge was washed well with methanol
  4. customEvaporation of the solvent from the ammoniacal fractions

Sources & evidence

ORD record
ord-0bca58efaa6247cdbcd0f4eafb99db1e
Source dataset
uspto-grants-2012_11
Patent number
US08304446B2

Reaction notes

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