Acetic Acid → HCID 66737108, compound

HRID 1641460Notes

Reaction equation

HRID 1641460 reaction equation
C(O)(=O)C.C(OC([NH:15][C:16]1[CH:20]=[C:19]([C:21]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:22])[N:18]([C:30]2[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][N:31]=2)[N:17]=1)=O)C1C=CC=CC=1>[H][H].[Pd]>[NH2:15][C:16]1[CH:20]=[C:19]([C:21]([O:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:22])[N:18]([C:30]2[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][N:31]=2)[N:17]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66737555HCID 66737555, compound

Product 1

HCID 66737108HCID 66737108, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

0.6 g of a 10% Pd—C powder was added to an acetic acid (50 ml) solution comprising 3.0 g of phenyl 3-benzyloxycarbonylamino-1-(3-chloropyridin-2-yl)-1H-5-pyrazolecarboxylate obtained by repeatedly carrying out the above step (5), followed by stirring in hydrogen atmosphere at room temperature for 12 hours. The reaction solution was subjected to filtration with celite, and then the filtrate and the liquid obtained after washing the celite were concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate) to obtain 1.1 g of crystals of the desired product (melting point: 140.4° C.).

Workup

  1. customobtained
  2. filtrationThe reaction solution was subjected to filtration with celite
  3. customthe filtrate and the liquid obtained
  4. washafter washing the celite
  5. concentrationwere concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-9754c92edfb94a3ca39ae2ff011c2925
Source dataset
uspto-grants-2012_02
Patent number
US08115006B2

Reaction notes

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