Potassium Carbonate → 2-Chloro-4-{[(3S)-1-methyl-5-oxo-3-pyrrolidinyl]amino}benzonitrile
Reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:11][C@H:12]([CH2:18][NH:19][CH3:20])[CH2:13][C:14](OC)=[O:15])[CH:6]=[CH:7][C:8]=1[C:9]#[N:10].C([O-])([O-])=O.[K+].[K+]>CC#N.CO>[Cl:2][C:3]1[CH:4]=[C:5]([NH:11][C@H:12]2[CH2:13][C:14](=[O:15])[N:19]([CH3:20])[CH2:18]2)[CH:6]=[CH:7][C:8]=1[C:9]#[N:10]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 68 °C
Procedure
A mixture of methyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-(methylamino)butanoate, hydrochloride (15.6 g., 49 mmole) and K2CO3 (325 mesh, 15.0 g, 110 mmole) in MeCN (120 mL) and MeOH (30 mL) was heated with stirring at 68° C. for 20 min. The solvents were evaporated, and the residue partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (2×), the combined EtOAc extracts were washed with H2O and brine, dried (MgSO4) and the solvent evaporated. The crude product (10.3 g) was triturated with Et2O, chilled and the solid filtered to give the titled compound (9.93 g, 81%). LC-MS (ES) m/e 250 (M+H)+.
Workup
- temperaturewas heated
- customThe solvents were evaporated
- customthe residue partitioned between EtOAc and H2O
- extractionThe aqueous layer was extracted with EtOAc (2×)
- washthe combined EtOAc extracts were washed with H2O and brine
- dry with materialdried (MgSO4)
- customthe solvent evaporated
- customThe crude product (10.3 g) was triturated with Et2O
- temperaturechilled
- filtrationthe solid filtered
Sources & evidence
- ORD record
- ord-08fefa167a5a462d81a2042317f88bc3
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816395B2
Reaction notes
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