Hydrogen chloride-ethyl acetate → HCID 67397695, compound

HRID 1426824Notes

Reaction equation

HRID 1426824 reaction equation
[F:1][CH:2]([F:34])[C:3]1[O:7][C:6]([S:8]([N:11]2[C:15]([C:16]3[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=3)=[C:14]([F:23])[C:13]([CH2:24][N:25](C)[C:26](=O)OC(C)(C)C)=[CH:12]2)(=[O:10])=[O:9])=[CH:5][CH:4]=1.C(OCC)(=O)C.[ClH:41]>C(OCC)(=O)C.CC(O)C>[ClH:41].[F:34][CH:2]([F:1])[C:3]1[O:7][C:6]([S:8]([N:11]2[C:15]([C:16]3[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=3)=[C:14]([F:23])[C:13]([CH2:24][NH:25][CH3:26])=[CH:12]2)(=[O:10])=[O:9])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67397054HCID 67397054, compound

Product 1

HCID 67397695HCID 67397695, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl {[1-{[5-(difluoromethyl)-2-furyl]sulfonyl}-4-fluoro-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate (154 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 1.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from a mixed solution of ethyl acetate-ethanol to give the title compound as a white solid (yield 96.3 mg, 72%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was recrystallized from a mixed solution of ethyl acetate-ethanol

Sources & evidence

ORD record
ord-4308df63735240ea9667464ad9442f50
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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