Water → HCID 178472238, compound

HRID 869710Notes

Reaction equation

HRID 869710 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=1.[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14](O)=[O:15].C(N=C=NC(C)C)(C)C.O>N1C=CC=CC=1>[CH2:19]([O:18][C:12](=[O:17])[CH2:13][C:14]([NH:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=1)=[O:15])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 12734DiisopropylcarbodiimideHCID 70615Monoethyl malonateHCID 178469278HCID 178469278, compound

Product 1

HCID 178472238HCID 178472238, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 5-aminopyrazole-3-carboxylate (5.00 g, 26.1 mmol) and ethyl hydrogen malonate (3.62 g, 27.4 mmol) in pyridine (130 mL) was added N,N′-diisopropylcarbodiimide (4.28 g, 33.9 mmol) at 0° C. After being stirred at same temperature, the reaction mixture was poured into water. The mixture was extracted with ethyl acetate and the organic layer was washed with saturated brine, dried over sodium sulfate, filtrated and concentrated in vacuo. The crude was purified by silica gel column chromatography (chloroform to chloroform:methanol=19:1) and triturated with diisopropyl ether to give ethyl 5-[(3-ethoxy-3-oxopropanoyl)amino]-1H-pyrazole-3-carboxylate. MS (APCI): m/z 270 (M+H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by silica gel column chromatography (chloroform to chloroform:methanol=19:1)
  7. customtriturated with diisopropyl ether

Sources & evidence

ORD record
ord-b5a3829d4c94486f8f1687c42961552e
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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