Ethyl 4-(furan-2-yl)-2,4-dioxobutanoate → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-furan-2-yl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 604422Notes

Reaction equation

HRID 604422 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5](=O)[CH2:6][C:7]([C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)=O)[CH3:2].[Cl:16][C:17]1[S:21][C:20]([C:22]2[O:26][N:25]=[C:24]([CH2:27][NH:28][NH2:29])[CH:23]=2)=[CH:19][CH:18]=1>C(O)(=O)C.O>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[N:28]([CH2:27][C:24]2[CH:23]=[C:22]([C:20]3[S:21][C:17]([Cl:16])=[CH:18][CH:19]=3)[O:26][N:25]=2)[N:29]=1)=[O:15])[CH3:2]

Participants

5

Reactant 2

HCID 3006753Ethyl 4-(furan-2-yl)-2,4-dioxobutanoateHCID 23033477HCID 23033477, compound

Product 1

HCID 602079551-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-furan-2-yl-1H-pyrazole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 550 mg 4-Furan-2-yl-2,4-dioxo-butyric acid ethyl ester and 601 mg [5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-hydrazine in 10 ml acetic acid was heated to 80° C. for 2 h. Then the reaction mixture was diluted with 20 ml water and extracted with ethyl acetate (3×100 ml). The combined organic layers were dried over MgSO4. The solvents were removed under reduced pressure and the residue was purified by silica gel chromatography eluting with a n-heptane:ethyl acetate gradient 100%->50%.

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customThe solvents were removed under reduced pressure
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with a n-heptane

Sources & evidence

ORD record
ord-316650b614c94ec892d59bf3b969580e
Source dataset
uspto-grants-2011_03
Patent number
US07910606B2

Reaction notes

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