N-methyl-2-pyrrolidone → HCID 136597042, compound

HRID 1476844Notes

Reaction equation

HRID 1476844 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([O: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].CN1C(=O)CCC1.[NH:34]([C:36](OCC)=[O:37])[NH2:35]>CCOC(C)=O>[O:37]=[C:36]1[NH:34][N:35]=[C:1]([C:3]2[N:4]=[C:5]([O: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

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 90387271HCID 90387271, compound

Product 1

HCID 136597042HCID 136597042, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
175 °C

Procedure

To a crude reaction mixture containing (R)-tert-butyl 2-(((3-cyanoisoquinolin-1-yl)oxy)methyl)pyrrolidine-1-carboxylate (0.749 g) was added NMP (2 mL) and ethyl hydrazinecarboxylate (0.883 g, 8.48 mmol). The reaction mixture was heated at 175° C. overnight and was subsequently cooled, diluted with EtOAc, and washed with saturated aqueous NH4Cl followed by water. The organic layer was separated and concentrated to give the title compound, which was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-065b1534b82b498485fe5ffd6fdc6f4e
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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