Hydrogen chloride-ethyl acetate → HCID 67398252, compound

HRID 1426832Notes

Reaction equation

HRID 1426832 reaction equation
C(O[C:6]([N:8]([CH2:10][C:11]1[C:12]([F:35])=[C:13]([C:28]2[C:29]([F:34])=[N:30][CH:31]=[CH:32][CH:33]=2)[N:14]([S:16]([C:19]2[CH:23]=[CH:22][S:21][C:20]=2[C:24]([O:26][CH3:27])=[O:25])(=[O:18])=[O:17])[CH:15]=1)C)=O)(C)(C)C.[C:36]([O:39]CC)(=[O:38])[CH3:37].Cl>C(OCC)(=O)C.CC(O)C>[C:24]([OH:26])(=[O:25])/[CH:20]=[CH:37]/[C:36]([OH:39])=[O:38].[F:35][C:12]1[C:11]([CH2:10][NH:8][CH3:6])=[CH:15][N:14]([S:16]([C:19]2[CH:23]=[CH:22][S:21][C:20]=2[C:24]([O:26][CH3:27])=[O:25])(=[O:18])=[O:17])[C:13]=1[C:28]1[C:29]([F:34])=[N:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67395940HCID 67395940, compound

Product 1

HCID 67398252HCID 67398252, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-{[4-{[(tert-butoxycarbonyl)(methyl)amino]methyl}-3-fluoro-2-(2-fluoropyridin-3-yl)-1H-pyrrol-1-yl]sulfonyl}thiophene-2-carboxylate (155 mg) in ethyl acetate (2 mL) and 2-propanol (1 mL) was added 4 mol/L hydrogen chloride-ethyl acetate solution (3 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a free base of the title compound as a colorless oil (yield 124 mg, 98%). A solution of the obtained free base (124 mg) in ethyl acetate (2 mL) was added dropwise to a solution of fumaric acid (32.9 mg) in ethanol (2 mL) and the mixture was concentrated under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate and ethanol to give the title compound as a white solid (yield 134 mg, 85%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with saturated aqueous sodium hydrogen carbonate solution
  3. extractionextracted with ethyl acetate
  4. extractionThe separated aqueous layer was extracted again with ethyl acetate
  5. washThe combined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6db7a05f79bf489aa8bb3919826cdfb2
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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