Hydrogen chloride-ethyl acetate → HCID 67397065, compound

HRID 1426806Notes

Reaction equation

HRID 1426806 reaction equation
[F:1][C:2]1[C:3]([CH2:29][N:30](C)[C:31](=O)OC(C)(C)C)=[CH:4][N:5]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([NH:25][CH2:26][CH2:27][OH:28])=[O:24])[CH:18]=2)(=[O:16])=[O:15])[C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1.C(OCC)(=O)C.[ClH:45]>C(OCC)(=O)C.CC(O)C>[ClH:45].[F:1][C:2]1[C:3]([CH2:29][NH:30][CH3:31])=[CH:4][N:5]([S:14]([C:17]2[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=2)[C:23]([NH:25][CH2:26][CH2:27][OH:28])=[O:24])(=[O:15])=[O:16])[C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67396431HCID 67396431, compound

Product 1

HCID 67397065HCID 67397065, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl ({4-fluoro-5-(2-fluoropyridin-3-yl)-1-[(3-{[(2-hydroxyethyl)amino]carbonyl}phenyl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate (226 mg) in ethyl acetate (3 mL) and 2-propanol (2 mL) was added 4 mol/L hydrogen chloride-ethyl acetate solution (6 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from ethanol to give the title compound as a white solid (yield 99 mg, 50%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-250f78ac63af4345914138ab8b58b6e4
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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