Hydrazinecarboxylic acid, ethyl ester → HCID 136596929, compound

HRID 1476840Notes

Reaction equation

HRID 1476840 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([NH:13][CH2:14][C@@H:15]2[CH2:19][CH2:18][CH2:17][N:16]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].[NH:27]([C:29](OCC)=[O:30])[NH2:28]>CCOC(C)=O>[O:30]=[C:29]1[NH:27][N:28]=[C:1]([C:3]2[N:4]=[C:5]([NH:13][CH2:14][C@@H:15]3[CH2:19][CH2:18][CH2:17][N:16]3[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:2]1

Participants

4

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 90387317HCID 90387317, compound

Product 1

HCID 136596929HCID 136596929, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
175 °C

Procedure

To a crude reaction mixture containing (S)-tert-butyl 2-(((3-cyanoisoquinolin-1-yl)amino)methyl)pyrrolidine-1-carboxylate (0.561 g) was added ethyl hydrazinecarboxylate (0.663 g, 6.36 mmol). The reaction mixture was heated at 175° C. overnight and was subsequently cooled, diluted with EtOAc, and washed with saturated aqueous NH4Cl. The aqueous and organic layers were separated. The organic layer was 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 saturated aqueous NH4Cl
  4. customThe aqueous and organic layers were separated
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-a10e351c62c64de1bf8496ec92d20ae5
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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