Water → 2-chloro-4-{[(3S)-1-ethyl-5-oxo-3-pyrrolidinyl]amino}benzonitrile

HRID 1160410Notes

Reaction equation

HRID 1160410 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:11][C@H:12]([CH2:18][NH:19][CH2:20][CH3:21])[CH2:13][C:14](OC)=[O:15])[CH:6]=[CH:7][C:8]=1[C:9]#[N:10].O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Cl:2][C:3]1[CH:4]=[C:5]([NH:11][C@H:12]2[CH2:13][C:14](=[O:15])[N:19]([CH2:20][CH3:21])[CH2:18]2)[CH:6]=[CH:7][C:8]=1[C:9]#[N:10]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 131728380Methyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-(ethylamino)butanoate, hydrochloride

Product 1

HCID 595161932-chloro-4-{[(3S)-1-ethyl-5-oxo-3-pyrrolidinyl]amino}benzonitrileYield 84.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-(ethylamino)butanoate, hydrochloride (4.0 g., 13.5 mmole) was redissolved in ethyl acetate (50 mL). Water was added (50 mL) and 10% sodium bicarbonate was added with stirring to bring the pH to 8.5. The organic layer was concentrated and redissolved in benzene (120 mL). The solution was heated with stirring at 75° C. for 6 h. The solvent was evaporated. The crude product was triturated with Et2O, chilled and the solid filtered to give the titled compound (3.0 g, 84%). LC-MS (ES) m/e 263 (M+H)+.

Workup

  1. additionwas added
  2. concentrationThe organic layer was concentrated
  3. dissolutionredissolved in benzene (120 mL)
  4. temperatureThe solution was heated
  5. stirringwith stirring at 75° C. for 6 h
  6. customThe solvent was evaporated
  7. customThe crude product was triturated with Et2O
  8. temperaturechilled
  9. filtrationthe solid filtered

Sources & evidence

ORD record
ord-1256a3ac72324cf88b7fdbf627272a99
Source dataset
uspto-grants-2010_10
Patent number
US07816395B2

Reaction notes

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