Acetic Anhydride → HCID 54068429, compound

HRID 1934693Notes

Reaction equation

HRID 1934693 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([C:10]1[CH:11]=[CH:12][C:13]([NH:30][C@H:31]2[CH2:35][CH2:34][NH:33][CH2:32]2)=[C:14]([CH:29]=1)[C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)=[O:16])#[N:9]>N1C=CC=CC=1>[C:1]([N:33]1[CH2:34][CH2:35][C@H:31]([NH:30][C:13]2[CH:12]=[CH:11][C:10]([C:8]#[N:9])=[CH:29][C:14]=2[C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)=[O:16])[CH2:32]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54010736HCID 54010736, compound

Product 1

HCID 54068429HCID 54068429, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (64 mg) was added to a solution of (S)-5-cyano-N-(3,4-dimethoxybenzyl)-2-(3-pyrrolidinylamino)benzamide (80 mg) in pyridine (1 mL). The mixture was stirred for an hour at ambient temperature. The mixture was partitioned between ethyl acetate and 1% hydrochloric acid. The organic layer was washed with an aqueous saturated sodiunn bicarbonate solution and brine. The resultant was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by a thin layer chromatography developed with 5% methanol in chloroform to give (S)-2-(1-acetylpyrrolidin-3-ylamino)-5-cyano-N-(3,4-dimethoxybenzyl)benzamide (62mg) as amorphous powders.

Workup

  1. customThe mixture was partitioned between ethyl acetate and 1% hydrochloric acid
  2. washThe organic layer was washed with an aqueous saturated sodiunn bicarbonate solution and brine
  3. dry with materialThe resultant was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a thin layer chromatography

Sources & evidence

ORD record
ord-7c0c4c9d8ee94f398fbeb7e2b2566b38
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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