N-methyl-2-pyrrolidone → HCID 136596959, compound

HRID 1476847Notes

Reaction equation

HRID 1476847 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([N:13]([CH3:26])[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].[NH:27]([C:29]([O:31]CC)=O)N.C[N:35]1C(=O)CCC1>CCOC(C)=O>[CH3:26][N:13]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[C:3]([C:1]2[NH:27][C:29](=[O:31])[NH:35][N:2]=2)[N:4]=1)[C@H:14]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:15]1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 90387398HCID 90387398, compound

Product 1

HCID 136596959HCID 136596959, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
175 °C

Procedure

To crude (S)-tert-butyl 3-((3-cyanoisoquinolin-1-yl)(methyl)amino)pyrrolidine-1-carboxylate (0.245 g) in NMP (1 mL) was added ethyl hydrazinecarboxylate (0.289 g, 2.78 mmol). The reaction mixture was heated at 175° C. for 2 days and was subsequently cooled, diluted with EtOAc, and washed with aqueous NH4Cl. The organic phase was separated, dried, and concentrated. The crude product was purified by HPLC to give the title compound (91 mg, 32% over 2 steps).

Workup

  1. temperaturewas subsequently cooled
  2. washwashed with aqueous NH4Cl
  3. customThe organic phase was separated
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-9f1054d98c724662934995995868a26a
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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