Methanol → HCID 86591156, compound

HRID 1070837Notes

Reaction equation

HRID 1070837 reaction equation
N[C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.ClC(O[CH2:11][C:12]1C=CC=[CH:14][CH:13]=1)=O.[C:18](=O)([O-:20])[O-:19].[K+].[K+].CO>C(Cl)Cl>[CH2:5]([NH:4][C:18](=[O:19])[OH:20])[C:6]1[CH:2]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH:3]1[CH:2]=[CH:6][CH:5]=[N:4]1

Participants

6

Reactant 4

HCID 887MethanolHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 178418806HCID 178418806, compound

Product 1

HCID 86591156HCID 86591156, compoundYield 177.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of amino-pyrazole (1.0 g, 5.95 mmol), prepared in step C, in 40 mL of CH2Cl2 at room temperature was added benzyl chloroformate (2.7 mL, 17.97 mmol). Solid potassium carbonate (4.1 g, 29.71 mmol) was added in one portion. After 24 h, methanol (5 mL) was added to the mixture, and stirring was continued for additional 2 h. Insoluble material was removed by filtration, and washed with methanol. The combined filtrate and rinsing were concentrated under reduced pressure to a thick syrup, which was separated by preparative TLC (CH2Cl2-MeOH=30:1). The silica was extracted with MeOH and CH2Cl2, the extracts were filtered and concentrated under reduced pressure to yield 1.16 g (64%) of the pyrazole benzyl carbamate as a solid (MH+=303.1).

Workup

  1. waitwas continued for additional 2 h
  2. customInsoluble material was removed by filtration
  3. washwashed with methanol
  4. washThe combined filtrate and rinsing
  5. concentrationwere concentrated under reduced pressure to a thick syrup, which
  6. customwas separated by preparative TLC (CH2Cl2-MeOH=30:1)
  7. extractionThe silica was extracted with MeOH and CH2Cl2
  8. filtrationthe extracts were filtered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff2febf174874c4bb32687919ddf33f5
Source dataset
uspto-grants-2005_06
Patent number
US06903131B2

Reaction notes

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