Ethyl 5-hydrazinyl-1,3-thiazole-4-carboxylate → ethyl 5-[4-(2-methoxy-2-oxoethyl)-3-methyl-5-(pyridin-2-yl)-1H-pyrazol-1-yl]-1,3-thiazole-4-carboxylate

HRID 563992Notes

Reaction equation

[NH:1]([C:3]1[S:7][CH:6]=[N:5][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[NH2:2].O=[C:14]([CH3:29])[CH:15]([C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)=O)[CH2:16][C:17]([O:19][CH3:20])=[O:18]>CO>[CH3:20][O:19][C:17](=[O:18])[CH2:16][C:15]1[C:14]([CH3:29])=[N:2][N:1]([C:3]2[S:7][CH:6]=[N:5][C:4]=2[C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:21]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1

Participants

Conditions

Temperature: 90 °C

Procedure

In a microwave reactor, 0.358 g (1.91 mmol) of ethyl 5-hydrazinyl-1,3-thiazole-4-carboxylate were added to 0.450 g (1.91 mmol) of methyl 4-oxo-3-(pyridin-2-ylcarbonyl)pentanoate in 4 ml methanol. In a microwave oven the closed vessel was heated at 90° C. for 2 hours. After removal of the solvent, the residue was extracted repeatedly with dichloromethane/water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue gave 0.508 g of product (61.8% of theory), NMR (CDCl3, 300 MHz): 1.12 (t, 3H); 2.35 (s, 3H); 3.66 (s, 2H); 3.69 (s, 3H); 4.08 (s, 3H); 7.19 (m, 1H); 7.32 (m, 1H); 7.66 (m, 1H); 8.51 (m, 1H); 8.72 (s, 1H).

Workup

customAfter removal of the solvent
extractionthe residue was extracted repeatedly with dichloromethane/water
dry with materialThe combined organic phases were dried over sodium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-72cf2f2bd8eb4815ae1b0cbd16ced40c
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067611B2

Reaction notes

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