3-Aminopyrrolidine → HCID 14989580, compound

HRID 1110062Notes

Reaction equation

HRID 1110062 reaction equation
[Cl:1][CH2:2][CH:3]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([F:17])=[C:12](F)[C:13]=2[F:15])[C:8](=[O:18])[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6]1)[CH3:4].[NH2:24][CH:25]1[CH2:29][CH2:28][NH:27][CH2:26]1>C(#N)C>[NH2:24][CH:25]1[CH2:29][CH2:28][N:27]([C:12]2[C:13]([F:15])=[C:14]3[C:9]([C:8](=[O:18])[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6][N:5]3[CH:3]([CH3:4])[CH2:2][Cl:1])=[CH:10][C:11]=2[F:17])[CH2:26]1

Participants

4

Reactant 2

HCID 1644013-AminopyrrolidineHCID 14989579HCID 14989579, compound

Product 1

HCID 14989580HCID 14989580, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

174 mg (0.5 mmol) of ethyl 1-(1-chloroprop-2-yl)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate was dissolved into 20 ml of acetonitrile. To this was added 215 mg (2.5 mmol) of 3-aminopyrrolidine and the mixture was reacted with heating under refluxing for 7 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=100:1-20:1) to obtain 172 mg of light yellow crystals of ethyl 7-(3-amino-1-pyrrolidinyl)-1-(1-chloroprop-2-yl)-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (Compound No. 1).

Workup

  1. customthe mixture was reacted
  2. temperaturewith heating
  3. temperatureunder refluxing for 7 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:1-20:1)

Sources & evidence

ORD record
ord-eea1067a11ac415797f4c92479c1bb99
Source dataset
uspto-grants-1994_06
Patent number
US05324735

Reaction notes

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