Trifluoroacetic acid → Cyclopropanesulfonic acid [4-(2-fluoro-4-iodo-phenylamino)-6-methoxy-1H-indazol-5-yl]-amide

HRID 79088Notes

Reaction equation

HRID 79088 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[C:12]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=3[F:34])[C:13]([NH:19][S:20]([CH:23]3[CH2:25][CH2:24]3)(=[O:22])=[O:21])=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[N:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:34][C:28]1[CH:29]=[C:30]([I:33])[CH:31]=[CH:32][C:27]=1[NH:26][C:12]1[C:13]([NH:19][S:20]([CH:23]2[CH2:24][CH2:25]2)(=[O:22])=[O:21])=[C:14]([O:17][CH3:18])[CH:15]=[C:16]2[C:11]=1[CH:10]=[N:9][NH:8]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67084397HCID 67084397, compound

Product 1

HCID 44603273Cyclopropanesulfonic acid [4-(2-fluoro-4-iodo-phenylamino)-6-methoxy-1H-indazol-5-yl]-amideYield 56.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-cyclopropanesulfonylamino-4-(2-fluoro-4-iodo-phenylamino)-6-methoxy-indazole-1-carboxylic acid tert-butyl ester (217 mg, 0.36 mmol) in DCM (5 mL) was treated with TFA (2 mL) and the reaction mixture stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and the residue triturated with diethyl ether to give the title compound as an off-white solid (102 mg, 52%). LCMS (method A): RT=10.17 [M+H]+=503. 1H NMR (DMSO-d6, 400 MHz): 12.92 (1 H, s), 8.72 (1 H, s), 7.60-7.52 (2 H, m), 7.34-7.24 (2 H, m), 6.71 (1 H, s), 6.53 (1 H, t, J=8.80 Hz), 3.84 (3 H, s), 2.53-2.46 (1 H, m), 0.84-0.73 (2 H, m), 0.72-0.66 (2 H, m).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-0fc90bedca1548d28561e7b807e24aca
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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