3-Acetamidopyrrolidine → HCID 20149301, compound

HRID 568824Notes

Reaction equation

HRID 568824 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:18]([OH:20])=[O:19])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[F:22].[C:23]([NH:26][CH:27]1[CH2:31][CH2:30][NH:29][CH2:28]1)(=[O:25])[CH3:24]>CN1CCCC1=O>[C:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:22])=[C:2]([N:29]4[CH2:30][CH2:31][CH:27]([NH:26][C:23](=[O:25])[CH3:24])[CH2:28]4)[CH:11]=3)[C:6](=[O:21])[C:7]([C:18]([OH:20])=[O:19])=[CH:8]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 5227153-AcetamidopyrrolidineHCID 13500610HCID 13500610, compound

Product 1

HCID 20149301HCID 20149301, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1.5 g 7-chloro-1-phenyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (product of Example 1(d)) in 20 ml of 1-methyl-2-pyrrolidinone at 115° C. is added 3 g of 3-acetamido-pyrrolidine. After stirring at 100° C. for 20 hours, the solvent is removed by reduced pressure to dryness. Ethanol is added to the residue and washed with ether and then diluted cold hydrochloric acid and then water. The solid is dried, yielding 1.60 g 1-phenyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-acetamido-1-pyrrolidinyl)-quinoline-3-carboxylic acid (9) ##STR43## R-phenyl).

Workup

  1. customthe solvent is removed by reduced pressure to dryness
  2. additionEthanol is added to the residue
  3. washwashed with ether
  4. additiondiluted cold hydrochloric acid
  5. customThe solid is dried

Sources & evidence

ORD record
ord-5143d1ab48244d498c606116a6fb5c9c
Source dataset
uspto-grants-1988_03
Patent number
US04730000

Reaction notes

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