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

HRID 1160406Notes

Reaction equation

HRID 1160406 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([CH2:20][NH:21][CH2:22][CH3:23])[CH2:12][C:13](OC(C)(C)C)=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].Cl.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]2[CH2:12][C:13](=[O:14])[N:21]([CH2:22][CH3:23])[CH2:20]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 595162371,1-dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-(ethylamino)butanoate

Product 1

HCID 595161932-chloro-4-{[(3S)-1-ethyl-5-oxo-3-pyrrolidinyl]amino}benzonitrileYield 54.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
65 °C

Procedure

A solution of 1,1-dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-(ethylamino)butanoate (5.66 g, 16.8 mmol), HCl (4M in dioxane, 40 mL) and MeOH (100 mL) was stirred at 65° C. for 2 h. After cooling, the reaction was concentrated. To the residue, K2CO3 (325 mesh, 6.6 g, 47.5 mmol) and MeOH (150 mL) were added and the reaction was stirred at 65° C. for 1 h. Solvent was removed and the residue was partitioned between EtOAc and H2O. The organic layer was dried over MgSO4 and concentrated to give the product as a white solid (2.4 g, 54%). LC-MS (ES) m/e 264.4 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction was concentrated
  3. customSolvent was removed
  4. customthe residue was partitioned between EtOAc and H2O
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-64e625d5c1734adb8737ae61691b7927
Source dataset
uspto-grants-2010_10
Patent number
US07816395B2

Reaction notes

Loading…