Hydrazinecarboxylic acid, ethyl ester → HCID 136596926, compound

HRID 1476917Notes

Reaction equation

HRID 1476917 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([O:9][C@H:10]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]2)[CH:6]=[CH:5][CH:4]=1)#[N:2].[NH:22]([C:24](OCC)=[O:25])[NH2:23]>CN1C(=O)CCC1.CCOC(C)=O>[O:25]=[C:24]1[NH:22][N:23]=[C:1]([C:3]2[N:8]=[C:7]([O:9][C@H:10]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)[CH:6]=[CH:5][CH:4]=2)[NH:2]1

Participants

5

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 90386995HCID 90386995, compound

Product 1

HCID 136596926HCID 136596926, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
175 °C

Procedure

To crude (S)-tert-butyl 3-((6-cyanopyridin-2-yl)oxy)pyrrolidine-1-carboxylate (1.044 g) in NMP (1.5 mL) was added ethyl hydrazinecarboxylate (0.752 g, 7.22 mmol). The reaction mixture was heated at 175° C. overnight and was subsequently cooled and diluted with EtOAc. The organic phase was washed with saturated aqueous NH4Cl, dried, and concentrated to give the title compound, which was used without further purification.

Workup

  1. temperaturewas subsequently cooled
  2. washThe organic phase was washed with saturated aqueous NH4Cl
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b8eb9a72e5c94664b87a3d2ab6ec637a
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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