Methylhydrazine → benzyl 3-(5-amino-1-methyl-1H-pyrazol-3-yl)-pyrrolidine-1-carboxylate

HRID 1034957Notes

Reaction equation

HRID 1034957 reaction equation
[C:1]([CH2:3][C:4]([CH:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7]1)=O)#[N:2].[CH3:21][NH:22][NH2:23]>C(O)C>[NH2:2][C:1]1[N:22]([CH3:21])[N:23]=[C:4]([CH:6]2[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:7]2)[CH:3]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 68892897Benzyl 3-(2-cyanoacetyl)-pyrrolidine-1-carboxylate

Product 1

HCID 69162082benzyl 3-(5-amino-1-methyl-1H-pyrazol-3-yl)-pyrrolidine-1-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of EXAMPLE 24B (1.9 g, 7 mmol) and methylhydrazine (367 μL, 7 mmol) in ethanol (15 mL) was heated at reflux for 4 hours. After cooling, the mixture was concentrated and the residue purified by flash chromatography on silica gel using 0-15% methanol in dichloromethane to give the title compound (1.78 g, 85%). MS(DCI): m/z 301 (M+1)+.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. customthe residue purified by flash chromatography on silica gel using 0-15% methanol in dichloromethane

Sources & evidence

ORD record
ord-c8c2f69170fe4c928fcde3dcf886bbe4
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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