Water → HCID 131734075, compound

HRID 714829Notes

Reaction equation

HRID 714829 reaction equation
CS(O[CH2:6][C:7]([N:10]1[CH:14]=[C:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:12]=[N:11]1)([CH3:9])[CH3:8])(=O)=O.[I-].[Na+].[CH3:25][S:26]([O-:28])=[O:27].[Na+].O>CN(C)C=O>[C:19]([O:18][C:16](=[O:17])[NH:15][C:13]1[CH:12]=[N:11][N:10]([C:7]([CH3:9])([CH3:8])[CH2:6][S:26]([CH3:25])(=[O:28])=[O:27])[CH:14]=1)([CH3:20])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 2733271Sodium methanesulfinateHCID 117840596HCID 117840596, compound

Product 1

HCID 131734075HCID 131734075, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of the crude 2-(4-((tert-butoxycarbonyl)amino)-1H-pyrazol-1-yl)-2-methylpropyl methanesulfonate (1.1 g) obtained in Step B of Example 114 in N,N-dimethylformamide (10 mL) were added sodium iodide (740 mg) and sodium methanesulfinate (1.0 g), and the mixture was stirred overnight at 140° C. To the reaction mixture was added water, and the mixture was 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 (hexane/ethyl acetate) to give the title compound (250 mg).

Workup

  1. extractionthe mixture was extracted 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 (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f42fb3f593c14956b5cd043d8cb809d0
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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