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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 563992
Notes
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Reaction equation

HRID 563992 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 55281999Ethyl 5-hydrazinyl-1,3-thiazole-4-carboxylateHCID 67005342Methyl 4-oxo-3-(pyridin-2-ylcarbonyl)pentanoate

Product 1

HCID 67005516ethyl 5-[4-(2-methoxy-2-oxoethyl)-3-methyl-5-(pyridin-2-yl)-1H-pyrazol-1-yl]-1,3-thiazole-4-carboxylateYield 68.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. customAfter removal of the solvent
  2. extractionthe residue was extracted repeatedly with dichloromethane/water
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes