Hydrochloric Acid → HCID 117840009, compound

HRID 714830Notes

Reaction equation

HRID 714830 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][N:11]([C:13]([CH3:20])([CH3:19])[CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=1)(C)(C)C.Cl.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH3:20][C:13]([N:11]1[CH:12]=[C:8]([NH2:7])[CH:9]=[N:10]1)([CH3:19])[CH2:14][S:15]([CH3:18])(=[O:16])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131734075HCID 131734075, compound

Product 1

HCID 117840009HCID 117840009, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To tert-butyl(1-(2-methyl-1-(methylsulfonyl)propan-2-yl)-1H-pyrazol-4-yl)carbamate (250 mg) obtained in Step C of Example 114 was added dropwise a solution of 4 M hydrogen chloride in ethyl acetate (4.0 mL), and the mixture was stirred at room temperature for 30 min. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (23 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-67efa65deb474897b941d5580ce7e08b
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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