Hydrochloric Acid → 7-(4-Bromo-2-fluoro-phenylamino)-benzo[d]isothiazole-6-carboxylic acid (2-hydroxy-ethoxy)-amide

HRID 79080Notes

Reaction equation

HRID 79080 reaction equation
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:18]=[CH:17][C:13]2[CH:14]=[N:15][S:16][C:12]=2[C:11]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=1[F:27])=[O:9])=C.Cl>CO>[OH:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:18]=[CH:17][C:13]2[CH:14]=[N:15][S:16][C:12]=2[C:11]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=1[F:27])=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866562527-(4-Bromo-2-fluoro-phenylamino)-benzo[d]isothiazole-6-carboxylic acid (2-vinyloxy-ethoxy)-amide

Product 1

HCID 446032707-(4-Bromo-2-fluoro-phenylamino)-benzo[d]isothiazole-6-carboxylic acid (2-hydroxy-ethoxy)-amideYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7-(4-bromo-2-fluoro-phenylamino)-benzo[d]isothiazole-6-carboxylic acid (2-vinyloxy-ethoxy)-amide (95 mg, 0.21 mmol) in MeOH (4 mL) was added a 1.0M aqueous solution of hydrochloric acid (0.42 mL). The reaction mixture was stirred at room temperature for 1 hour before being concentrated in vacuo. The resultant residue was taken up in ethyl acetate, washed with a saturated aqueous solution of sodium hydrogen carbonate then brine, dried (Na2SO4), filtered and evaporated in vacuo. The resultant residue was subjected to flash chromatography (Si—PPC, gradient 0% to 100%, ethyl acetate in DCM) to afford the title compound as a yellow solid (62 mg, 70%). LCMS (method A): RT=9.51 min, [M+H]+=426/428. 1H NMR (CDCl3, 400 MHz) 9.37 (1 H, s), 8.85 (1 H, s), 8.76 (1 H, s), 7.51 (1 H, d, J=8.40 Hz), 7.43 (1 H, d, J=8.40 Hz), 7.34-7.29 (1 H, m), 7.28 (1 H, d, J=8.75 Hz), 7.02 (1 H, t, J=8.46 Hz), 4.10 (2 H, t, J=4.09 Hz), 3.91 (1 H, s), 3.80 (2 H, s).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. washwashed with a saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materialbrine, dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-cf870f71779e48468b0c76d62ab703e7
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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