Trifluoroacetic acid → HCID 56962531, compound

HRID 1037541Notes

Reaction equation

HRID 1037541 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17](=[O:20])[NH:18][CH3:19])=[C:15]3[C:10]([CH:11]=[C:12]([N:24]([S:37]([CH3:40])(=[O:39])=[O:38])[CH:25]4[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26]4)[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:18][CH3:19])=[O:20])=[C:15]3[C:10]([CH:11]=[C:12]([N:24]([S:37]([CH3:40])(=[O:39])=[O:38])[CH:25]4[CH2:29][CH2:28][NH:27][CH2:26]4)[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67776620HCID 67776620, compound

Product 1

HCID 56962531HCID 56962531, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl 3-{[2-(4-bromophenyl)-5-cyclopropyl-3-(methylcarbamoyl)-2H-indazol-6-yl](methylsulfonyl)amino}pyrrolidine-1-carboxylate (12 mg, 0.019 mmol) in DCM (0.5 mL) was added trifluoroacetic acid (50 μL) and the mixture was stirred at 40° C. for 40 min. The mixture was cooled to RT, washed with saturated aqueous sodium bicarbonate (0.5 mL), dried (MgSO4) and concentrated to dryness. The residue was purified by preparative LCMS (5-100% ACN in 0.1% aqueous formic acid) to afford 2-(4-bromophenyl)-5-cyclopropyl-N-methyl-6-[(methylsulfonyl)(pyrrolidin-3-yl)amino]-2H-indazole-3-carboxamide as a white solid (4.4 mg, 44%).

Workup

  1. temperatureThe mixture was cooled to RT
  2. washwashed with saturated aqueous sodium bicarbonate (0.5 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by preparative LCMS (5-100% ACN in 0.1% aqueous formic acid)

Sources & evidence

ORD record
ord-52019b8de0e54ee3a195712e2e7b9521
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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