Hydrogen chloride-ethyl acetate → HCID 67396620, compound

HRID 1426802Notes

Reaction equation

HRID 1426802 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9]([N:12]2[C:16]([C:17]3[C:18]([C:23]#[N:24])=[N:19][CH:20]=[CH:21][CH:22]=3)=[C:15]([F:25])[C:14]([CH2:26][N:27](C)[C:28](=O)OC(C)(C)C)=[CH:13]2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(OCC)(=O)C.[ClH:42]>C(OCC)(=O)C.CC(O)C>[ClH:42].[C:1]([C:3]1[CH:4]=[C:5]([S:9]([N:12]2[CH:13]=[C:14]([CH2:26][NH:27][CH3:28])[C:15]([F:25])=[C:16]2[C:17]2[C:18]([C:23]#[N:24])=[N:19][CH:20]=[CH:21][CH:22]=2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67397564HCID 67397564, compound

Product 1

HCID 67396620HCID 67396620, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl {[1-[(3-cyanophenyl)sulfonyl]-5-(2-cyanopyridin-3-yl)-4-fluoro-1H-pyrrol-3-yl]methyl}methylcarbamate (401 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 17 hr. The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from a mixed solvent of ethanol and water to give the title compound as a white solid (yield 276 mg, 79%).

Workup

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

Sources & evidence

ORD record
ord-d24101e30a5844d3a32e138fbee6176e
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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