Ammonia methanol → tert-butyl {[1-{[5-(aminocarbonyl)-2-furyl]sulfonyl}-4-fluoro-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate

HRID 1426738Notes

Reaction equation

HRID 1426738 reaction equation
[C:1]([O:5][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](OC)=[O:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:15]=1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[NH3:38]>CO>[NH2:38][C:24]([C:22]1[O:23][C:19]([S:16]([N:14]2[C:13]([C:28]3[C:29]([F:34])=[N:30][CH:31]=[CH:32][CH:33]=3)=[C:12]([F:35])[C:11]([CH2:10][N:8]([CH3:9])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:15]2)(=[O:17])=[O:18])=[CH:20][CH:21]=1)=[O:25]

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 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 67396181tert-butyl {[1-{[5-(aminocarbonyl)-2-furyl]sulfonyl}-4-fluoro-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamateYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 (443 mg) in methanol (5 mL) was added 8 mol/L ammonia methanol solution (1 mL) at room temperature and the mixture was stirred for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→2:3) to give the title compound as a pale-yellow oil (yield 330 mg, 77%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→2:3)

Sources & evidence

ORD record
ord-923847fb0f0e4630b5b3391d8bd3edfd
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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