Hydrochloric Acid → 7-(2-Fluoro-4-methylsulfanyl-phenylamino)-benzo[d]isothiazole-6-carboxylic acid ((R)-2,3-dihydroxy-propoxy)-amide

HRID 79075Notes

Reaction equation

HRID 79075 reaction equation
CC1(C)[O:6][C@@H:5]([CH2:7][O:8][NH:9][C:10]([C:12]2[CH:20]=[CH:19][C:15]3[CH:16]=[N:17][S:18][C:14]=3[C:13]=2[NH:21][C:22]2[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][C:23]=2[F:30])=[O:11])[CH2:4][O:3]1.Cl>CO>[OH:6][C@H:5]([CH2:4][OH:3])[CH2:7][O:8][NH:9][C:10]([C:12]1[CH:20]=[CH:19][C:15]2[CH:16]=[N:17][S:18][C:14]=2[C:13]=1[NH:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][C:23]=1[F:30])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86656250HCID 86656250, compound

Product 1

HCID 446032677-(2-Fluoro-4-methylsulfanyl-phenylamino)-benzo[d]isothiazole-6-carboxylic acid ((R)-2,3-dihydroxy-propoxy)-amideYield 26.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7-(2-fluoro-4-methylsulfanyl-phenylamino)-benzo[d]isothiazole-6-carboxylic acid ((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-amide (170 mg, 0.37 mmol) in MeOH (2 mL) was added a 1.0M aqueous solution of hydrochloric acid (0.80 mL). The reaction mixture was stirred at room temperature for 1 hour before being concentrated in vacuo. The residue was taken up in ethyl acetate, washed with a saturated aqueous solution of sodium hydrogen carbonate followed by brine, dried (Na2SO4), filtered and evaporated in vacuo. The resultant residue was subjected to flash chromatography (Si—PPC, gradient 0% to 100%, MeOH in DCM) to afford the title compound as a yellow solid (42 mg, 26%). LCMS (Method A): RT=8.80 min, [M+H]+=478. 1H NMR (CD3OD) 8.81 (1 H, s), 7.63-7.56 (2 H, m), 7.12-7.04 (3 H, m), 4.10-4.04 (1 H, m), 3.98-3.86 (2 H, m), 3.64-3.55 (2 H, m), 2.50 (3 H, s).

Workup

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

Sources & evidence

ORD record
ord-a279f1cc754942d9bed6d4e197bca7b7
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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