N-methyl-2-pyrrolidone → HCID 136597051, compound

HRID 1476799Notes

Reaction equation

HRID 1476799 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([NH:13][C@H:14]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]2)[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].CN1C(=O)CCC1.[NH:33]([C:35](OCC)=[O:36])[NH2:34]>CCOC(C)=O>[O:36]=[C:35]1[NH:33][N:34]=[C:1]([C:3]2[N:4]=[C:5]([NH:13][C@H:14]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]3)[C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:2]1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 90386987HCID 90386987, compound

Product 1

HCID 136597051HCID 136597051, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
175 °C

Procedure

To a crude reaction mixture containing (S)-tert-butyl 3-((3-cyanoisoquinolin-1-yl)amino)pyrrolidine-1-carboxylate (717 mg) was added NMP (2 mL) and ethyl hydrazinecarboxylate (883 mg, 8.484 mmol). The reaction mixture was heated at 175° C. overnight and was subsequently cooled, diluted with EtOAc, and washed with aqueous NH4Cl. The organic layer was separated and concentrated to give the title compound, which was used directly in the next step.

Workup

  1. customTo a crude reaction mixture
  2. temperaturewas subsequently cooled
  3. washwashed with aqueous NH4Cl
  4. customThe organic layer was separated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1db20918b08e41208c25a43a5aa72dd9
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

Loading…