Methylhydrazine → HCID 9928201, compound

HRID 1835159Notes

Reaction equation

HRID 1835159 reaction equation
[CH3:1][CH:2]([CH3:27])[CH2:3][C:4]([C:6]1[C:10]([C:11](OCC)=[O:12])=[CH:9][N:8]([CH2:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)[N:7]=1)=O.[CH3:28][NH:29][NH2:30]>C(O)C>[CH3:28][N:29]1[C:11](=[O:12])[C:10]2=[CH:9][N:8]([CH2:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)[N:7]=[C:6]2[C:4]([CH2:3][CH:2]([CH3:27])[CH3:1])=[N:30]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 23503226HCID 23503226, compound

Product 1

HCID 9928201HCID 9928201, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-(3-methyl-1-oxobutyl)-1-(1-naphthalenylmethyl)-1H-pyrazole-4-carboxylate (1.8 g) and methylhydrazine (0.6 ml) in ethanol (20 ml) were heated underreflux for 16 hours. The solution was cooled and evaporated to a solid, which was purified by chromatography on silica (ethyl acetate:isohexane 2:3) followed by crystallisation from ethyl acetate/cyclohexane to give 2,5-dihydro-5-methyl-7-(2-methylpropyl)-2-(1-naphthalenylmethyl)-4H-pyrazolo[3,4-d]pyridazin-4-one (0.43 g).

Workup

  1. temperatureThe solution was cooled
  2. customevaporated to a solid, which
  3. customwas purified by chromatography on silica (ethyl acetate:isohexane 2:3)
  4. customfollowed by crystallisation from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-0f4c7da96f3c4b13a208ef220e24484a
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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