N-methyl-2-pyrrolidone → HCID 136596918, compound

HRID 1476842Notes

Reaction equation

HRID 1476842 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 90386900HCID 90386900, compound

Product 1

HCID 136596918HCID 136596918, 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)oxy)methyl)pyrrolidine-1-carboxylate (0.562 g) was added NMP (2 mL) followed by 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 brine. The organic layer was separated, dried over Na2SO4, 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 brine
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7de1555aa5fe4fae9a69459171a12bd5
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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