Methanol → HCID 67189704, compound

HRID 546046Notes

Reaction equation

HRID 546046 reaction equation
[CH2:1]([S:3]([N:6]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[N:7]1)(=[O:5])=[O:4])[CH3:2].CO.[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([S:3]([N:6]1[CH:10]=[CH:9][C:8]([NH2:11])=[N:7]1)(=[O:5])=[O:4])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 67189366HCID 67189366, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67189704HCID 67189704, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Ethanesulfonyl-3-nitro-1H-pyrazole (139 mg, 0.68 mmol) was dissolved in ethyl acetate (3 mL) and methanol (3 mL) was added. Palladium, 10 wt. % on carbon, wet (˜50 mg) was added to the mixture. The vial was charged with hydrogen gas (via balloon) and the mixture was stirred for 16 h at 25° C. The mixture was passed through a plug of celite and concentrated in vacuo followed by purification by flash column chromatography (Merck silica gel 60, 40-63 μm; 25% ethyl acetate/hexanes to 90% ethyl acetate/hexanes) afforded 1-ethanesulfonyl-1H-pyrazol-3-ylamine (88 mg, 74%) as a faintly yellow wax: ESI-LRMS m/e calcd for C5H9N3O2S [M+] 175.04, found 176.3 [M+H+], 351.2 [2M+H+].

Workup

  1. concentrationconcentrated in vacuo
  2. customfollowed by purification by flash column chromatography (Merck silica gel 60, 40-63 μm; 25% ethyl acetate/hexanes to 90% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4d25c243154f4d68849128f19fdd8707
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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