Ethyl 4-(dimethylamino)-2-oxo-but-3-enoate → ethyl 1-cyclopropyl-1H-pyrazole-5-carboxylate

HRID 873848Notes

Reaction equation

HRID 873848 reaction equation
[CH:1]1([NH:4][NH2:5])[CH2:3][CH2:2]1.CN(C)[CH:8]=[CH:9][C:10](=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12]>>[CH:1]1([N:4]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=[N:5]2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 2777802Ethyl 4-(dimethylamino)-2-oxo-but-3-enoateHCID 19594968Cyclopropylhydrazine

Product 1

HCID 117702698ethyl 1-cyclopropyl-1H-pyrazole-5-carboxylate

Procedure

The title compound was prepared in analogy to the procedure described in Step 17.3 using cyclopropylhydrazine (Step 17.2) and ethyl 4-(Dimethylamino)-2-oxobut-3-enoate at 125° C. for 8 hr. The crude product was purified by silica gel column chromatography (hexane/EtOAc 2.5-45%). tR: 4.40 min (HPLC 1); tR: 0.91 min (LC-MS 2); ESI-MS: 181 [M+H]+ (LC-MS 2); Rf=0.85 (hexane/EtOAc 1:1).

Workup

  1. customThe crude product was purified by silica gel column chromatography (hexane/EtOAc 2.5-45%)

Sources & evidence

ORD record
ord-0ee407c937fd4278ab4c03262e89f49f
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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