N-methyl-2-pyrrolidone → HCID 136597021, compound

HRID 1476920Notes

Reaction equation

HRID 1476920 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([O:9][C@H:10]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]2)[C:6]([CH3:22])=[CH:5][CH:4]=1)#[N:2].C[N:24]1[C:28](=[O:29])CCC1.[NH:30](C(OCC)=O)N>CCOC(C)=O>[CH3:22][C:6]1[C:7]([O:9][C@H:10]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:11]2)=[N:8][C:3]([C:1]2[NH:30][C:28](=[O:29])[NH:24][N:2]=2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 90386938HCID 90386938, compound

Product 1

HCID 136597021HCID 136597021, compoundYield 4.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
175 °C

Procedure

To the reaction mixture containing (S)-tert-butyl 3-((6-cyano-3-methylpyridin-2-yl)oxy)pyrrolidine-1-carboxylate (1.095 g) was added NMP (1.5 mL) and ethyl hydrazinecarboxylate (0.752 g, 7.22 mmol). The mixture was heated at 175° C. for 1.5 days and was subsequently cooled and diluted with EtOAc. The organic phase was washed with aqueous NH4Cl, dried, and concentrated. The crude product was purified by preparative HPLC eluting with a gradient of 35-60% ACN in water (acid mode) to give the title compound (0.042 g, 4.4% over 2 steps).

Workup

  1. temperaturewas subsequently cooled
  2. washThe organic phase was washed with aqueous NH4Cl
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative HPLC
  6. washeluting with a gradient of 35-60% ACN in water (acid mode)

Sources & evidence

ORD record
ord-e080817a8b1d4b2cb87816d438b4ad58
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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