Benzoyl chloride → N-(1-(3-fluoro-4-methoxyphenyl)-5-oxopyrrolidin-3-yl)benzamide

HRID 1993381Notes

Reaction equation

HRID 1993381 reaction equation
[NH2:1][CH:2]1[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([F:15])[CH:8]=2)[C:4](=[O:16])[CH2:3]1.C([O-])([O-])=O.[K+].[K+].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[F:15][C:9]1[CH:8]=[C:7]([N:5]2[C:4](=[O:16])[CH2:3][CH:2]([NH:1][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:6]2)[CH:12]=[CH:11][C:10]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 435211184-Amino-1-(3-fluoro-4-methoxyphenyl)pyrrolidin-2-one

Product 1

HCID 68419077N-(1-(3-fluoro-4-methoxyphenyl)-5-oxopyrrolidin-3-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-amino-1-(3-fluoro-4-methoxyphenyl)-pyrrolidin-2-one (Step 2, 0.8 g, 3.57 mmol) and K2CO3 (0.99 g, 7.14 mmol) in 20 mL of CH2Cl2 was added benzoyl chloride (0.75 g, 5.35 mmol). The reaction was stirred at RT for 16 h. The solid in the reaction was removed by filtration and the filtrate was diluted with 20 mL of CH2Cl2. The resulted solution was washed with 20 mL of satd. NaHCO3 followed by 20 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (30% to 100% EtOAc/hexane) to provide the title compound as a white solid. MS (ESI pos. ion) m/z: 329.4 (M+H). Calc'd Exact Mass for C18H17FN2O3: 328.34.

Workup

  1. customThe solid in the reaction was removed by filtration
  2. additionthe filtrate was diluted with 20 mL of CH2Cl2
  3. washThe resulted solution was washed with 20 mL of satd
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (30% to 100% EtOAc/hexane)

Sources & evidence

ORD record
ord-2e18f0d543a0499eaf223ade9f11dcab
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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