Hydrochloric Acid → HCID 44603271, compound

HRID 79082Notes

Reaction equation

HRID 79082 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]([I: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]([I:26])=[CH:22][C:21]=1[F:27])=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 575215067-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-6-carboxylic acid (2-vinyloxy-ethoxy)-amide

Product 1

HCID 44603271HCID 44603271, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7-(2-fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-6-carboxylic acid (2-vinyloxy-ethoxy)-amide (187 mg, 0.37 mmol) in MeOH (4 mL) was added a 1.0M aqueous solution of hydrochloric acid (0.75 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 (128 mg, 72%). LCMS (method A): RT=9.81 min, [M+H]+=474. 1H NMR (CDCl3, 400 MHz) 9.33 (1 H, s), 8.86 (1 H, s), 8.77 (1 H, s), 7.55-7.40 (4 H, m), 6.84 (1 H, t, J=8.30 Hz), 4.10 (2 H, t, J=4.16 Hz), 3.91 (1 H, t, J=6.45 Hz), 3.80 (2 H, t, J=4.55 Hz).

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-2bbfddd1bae04fd79401747c159e1452
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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