Ethyl Acetate → HCID 67395815, compound

HRID 1426839Notes

Reaction equation

HRID 1426839 reaction equation
[F:1][C:2]1[C:3]([CH2:25][N:26](C)[C:27](=O)OC(C)(C)C)=[CH:4][N:5]([S:14]([C:17]2[CH:18]=[N:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=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:35]([O:38]CC)(=[O:37])[CH3:36].Cl.[C:42]([O:45]CC)(=[O:44])[CH3:43]>C(O)C>[C:42]([OH:45])(=[O:44])/[CH:43]=[CH:36]/[C:35]([OH:38])=[O:37].[F:1][C:2]1[C:3]([CH2:25][NH:26][CH3:27])=[CH:4][N:5]([S:14]([C:17]2[CH:18]=[N:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21866389Hydrogen chloride-ethyl acetateHCID 69097918HCID 69097918, compound

Product 1

HCID 67395815HCID 67395815, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl ({4-fluoro-5-(2-fluoropyridin-3-yl)-1-[(6-methoxypyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate (124 mg) was dissolved in ethyl acetate (1 mL) and ethanol (1 mL), and 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added. After stirring at room temperature for 2 hr, the reaction mixture was concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound as a free base (57.1 mg). A solution of the obtained free base (57.1 mg) in ethyl acetate (2 mL) was added dropwise to a solution of fumaric acid (24 mg) in ethanol (2 mL), and the mixture was concentrated under reduced pressure. The obtained crystal was recrystallized from a mixed solvent of ethanol-water=20:1 to give the title compound as colorless crystals (yield 24.4 mg, 33%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionSaturated aqueous sodium hydrogen carbonate solution was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-65a0df51c2c147999dc784b0983495a8
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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