Hydrogen chloride-ethyl acetate → Methyl 5-({3-fluoro-2-(2-fluoropyridin-3-yl)-4-[(methylamino)methyl]-1H-pyrrol-1-yl}sulfonyl)-2-furoate hydrochloride

HRID 1426819Notes

Reaction equation

HRID 1426819 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[O:23][C:22]([C:24]([O:26][CH3:27])=[O:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:15]=1)C)=O)(C)(C)C.C(OCC)(=O)C.[ClH:42]>C(OCC)(=O)C.CC(O)C>[ClH:42].[F:35][C:12]1[C:11]([CH2:10][NH:8][CH3:6])=[CH:15][N:14]([S:16]([C:19]2[O:23][C:22]([C:24]([O:26][CH3:27])=[O:25])=[CH:21][CH:20]=2)(=[O:17])=[O:18])[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 67395998Methyl 5-{[4-{[(tert-butoxycarbonyl)(methyl)amino]methyl}-3-fluoro-2-(2-fluoropyridin-3-yl)-1H-pyrrol-1-yl]sulfonyl}-2-furoate

Product 1

HCID 67397052Methyl 5-({3-fluoro-2-(2-fluoropyridin-3-yl)-4-[(methylamino)methyl]-1H-pyrrol-1-yl}sulfonyl)-2-furoate hydrochlorideYield 78%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 5-{[4-{[(tert-butoxycarbonyl)(methyl)amino]methyl}-3-fluoro-2-(2-fluoropyridin-3-yl)-1H-pyrrol-1-yl]sulfonyl}-2-furoate (260 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 recrystallized from a mixed solvent of ethyl acetate-ethanol to give the title compound as a white solid (yield 177 mg, 78%).

Workup

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

Sources & evidence

ORD record
ord-0c57d9e88eb545408ec7a6dd2b0d0bc7
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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