Hydrochloric Acid → 4-(4-Bromo-2-fluoro-phenylamino)-1H-indazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide

HRID 79061Notes

Reaction equation

HRID 79061 reaction equation
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[C:11]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=2[F:27])=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][N:14]=[CH:13]2)=[O:9])=C.Cl>CO>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[C:11]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=2[F:27])=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][N:14]=[CH:13]2)=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86656246HCID 86656246, compound

Product 1

HCID 446031444-(4-Bromo-2-fluoro-phenylamino)-1H-indazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(4-bromo-2-fluorophenylamino)-1H-indazole-5-carboxylic acid (2-vinyloxy-ethoxy)-amide (96 mg, 0.22 mmol) in methanol (5 mL) was added hydrochloric acid (1 mL, 1N, 1 mmol). The reaction was stirred at room temperature for 30 minutes before being concentrated in vacuo. The resultant residue was dissolved in methanol (2 mL) and a few drops of water added causing the product to precipitate. The product was collected by filtration and dried in vacuo to yield the title compound as an off white solid (50 mg, 55%). LCMS (Method A): RT=7.99 min, [M+H]+=409/411. 1H NMR (DMSO-d6, 400 MHz) 13.20 (1H, s), 11.61 (1H, s), 9.95 (1H, s), 7.58 (1H, dd, J=10.48, 2.24 Hz), 7.47 (1H, d, J=8.77 Hz), 7.29 (1H, ddd, J=8.60, 2.21, 1.05 Hz), 7.23 (1H, s), 7.08 (1H, t, J=8.81 Hz), 7.01 (1H, d, J=8.81 Hz), 4.68 (1H, s), 3.86 (2H, t, J=4.95 Hz), 3.56 (3H, s).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. dissolutionThe resultant residue was dissolved in methanol (2 mL)
  3. additiona few drops of water added
  4. customto precipitate
  5. filtrationThe product was collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-795532c82bf3436db0d3d5140cf94277
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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