Trifluoroacetic acid → HCID 58054473, compound

HRID 1808593Notes

Reaction equation

HRID 1808593 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]([CH2:26][OH:27])[CH:22]=[CH:23][CH:24]=3)[C:19]([N:28]([S:38]([C:41]3[S:42][C:43]([Cl:46])=[CH:44][CH:45]=3)(=[O:40])=[O:39])[S:29]([C:32]3[S:33][C:34]([Cl:37])=[CH:35][CH:36]=3)(=[O:31])=[O:30])=[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]([CH2:26][OH:27])[CH:22]=[CH:23][CH:24]=3)[C:19]([N:28]([S:38]([C:41]3[S:42][C:43]([Cl:46])=[CH:44][CH:45]=3)(=[O:40])=[O:39])[S:29]([C:32]3[S:33][C:34]([Cl:37])=[CH:35][CH:36]=3)(=[O:31])=[O:30])=[N:18]2)[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86644814HCID 86644814, compound

Product 1

HCID 58054473HCID 58054473, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl[(3-{[3-{bis[(5-chloro-2-thienyl)sulfonyl]amino}-4-(hydroxymethyl)-1H-indazol-1-yl]methyl}phenyl)methyl]carbamate (for a preparation see Intermediate 71) (93 mg, 0.125 mmol) was dissolved in dichloromethane (0.5 mL), trifluoroacetic acid (0.125 mL) was added to the solution and stirred for 1 h under nitrogen. The reaction mixture was concentrated under a stream of nitrogen and the residue was dissolved in methanol and loaded onto a methanol pre-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 (53 mg, 66%) as a white solid. LCMS (System A) RT=0.89 min, ES+ve m/z 643/645 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under a stream of nitrogen
  2. dissolutionthe 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-697ced74cac84d438beb1773e92af5ec
Source dataset
uspto-grants-2013_01
Patent number
US08357716B2

Reaction notes

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