Trifluoroacetic acid → N-[4-[(2-Fluoro-4-iodophenyl)amino]-1H-indazol-5-yl]cyclopropanesulfonamide

HRID 79086Notes

Reaction equation

HRID 79086 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[C:12]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=3[F:32])[C:13]([NH:17][S:18]([CH:21]3[CH2:23][CH2:22]3)(=[O:20])=[O:19])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:32][C:26]1[CH:27]=[C:28]([I:31])[CH:29]=[CH:30][C:25]=1[NH:24][C:12]1[C:13]([NH:17][S:18]([CH:21]2[CH2:23][CH2:22]2)(=[O:20])=[O:19])=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[N:9][NH:8]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67083644HCID 67083644, compound

Product 1

HCID 44603272N-[4-[(2-Fluoro-4-iodophenyl)amino]-1H-indazol-5-yl]cyclopropanesulfonamideYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-cyclopropanesulfonylamino-4-(2-fluoro-4-iodo-phenylamino)-indazole-1-carboxylic acid tert-butyl ester (206 mg, 0.36 mmol) in DCM (8 mL) was added TFA (1 mL) and the reaction mixture stirred at room temperature for 2 hours. Additional TFA (1 mL) was added and stirring continued for a further 1 hour before the reaction mixture was concentrated in vacuo and the residue azeotroped with DCM, methanol and then DCM again. The resultant residue was triturated with diethyl ether, the solid filtered off and dried under vacuum at 40° C. to give the title compound as a yellow solid (83 mg, 49%). LCMS (Method A): RT=10.03 [M+H]+=437, 1H NMR (DMSO-d6, 400 MHz): 13.14 (1 H, s), 9.07 (1 H, s), 7.80 (1 H, s), 7.57 (1 H, dd, J=10.84, 1.96 Hz), 7.39 (1 H, s), 7.31 (1 H, d, J=8.74 Hz), 7.25-7.20 (2 H, m), 6.45 (1 H, t, J=8.84 Hz), 2.40-2.32 (1 H, m), 0.75-0.62 (4 H, m), −0.05 (1 H, t, J=3.33 Hz).

Workup

  1. stirringstirring
  2. waitcontinued for a further 1 hour before the reaction mixture
  3. concentrationwas concentrated in vacuo
  4. customthe residue azeotroped with DCM, methanol
  5. customThe resultant residue was triturated with diethyl ether
  6. filtrationthe solid filtered off
  7. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-738a6b0dc4cd4de899ee2fb5bbeb3231
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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