Methylhydrazine → HCID 66633572, compound

HRID 2359926Notes

Reaction equation

HRID 2359926 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([C:14](=O)[CH2:15][C:16](=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:11]([CH3:13])[N:12]=2)[CH:5]=[N:6][CH:7]=1.[CH3:24][NH:25][NH2:26]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([C:14]3[CH:15]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:25]([CH3:24])[N:26]=3)=[C:11]([CH3:13])[N:12]=2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 66633701HCID 66633701, compound

Product 1

HCID 66633572HCID 66633572, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-2,4-dioxobutanoate (6.9 g, 20.5 mmol) and methylhydrazine (0.65 g, 20.5 mmol) were heated in ethanol (250 ml) under reflux for 2 h. The product formed was filtered off with suction and the solvent of the filtrate was removed under reduced pressure. The residue was chromatographed on silica gel (cyclohexane/ethyl acetate eluent). This gave a total of 1.24 g (17% of theory) of ethyl 3-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-1H-pyrazole-5-carboxylate. As a by-product, 4.8 g (67% of theory) of ethyl 5-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-1H-pyrazole-3-carboxylate were obtained.

Workup

  1. temperatureunder reflux for 2 h
  2. customThe product formed
  3. filtrationwas filtered off with suction
  4. customthe solvent of the filtrate was removed under reduced pressure
  5. customThe residue was chromatographed on silica gel (cyclohexane/ethyl acetate eluent)

Sources & evidence

ORD record
ord-9fa4e2c9c7dc4a2d9ec63dd71db86b94
Source dataset
uspto-grants-2014_04
Patent number
US08686004B2

Reaction notes

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