HCID 1516512, compound → HCID 70395241, compound

HRID 477024Notes

Reaction equation

HRID 477024 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[NH2:22][CH2:23][C@H:24]1[C@@H:28]([CH3:29])[CH2:27][NH:26][CH2:25]1>C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:26]2[CH2:27][C@H:28]([CH3:29])[C@H:24]([CH2:23][NH2:22])[CH2:25]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 1516512HCID 1516512, compoundHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 70395241HCID 70395241, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.22 g), cis-3-aminomethyl-4-methylpyrrolidine (1.68 g), and acetonitrile (30 ml) was refluxed for 4.5 hours. The reaction mixture was concentrated to dryness under reduced pressure. The resulting crude crystals were recrystallized from ethanol to give 5-amino-7-(cis-3-aminomethyl-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.3 g), recrystallized from ethanol-chloroform, m.p. 221°-223° C.

Workup

  1. temperaturewas refluxed for 4.5 hours
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  3. customThe resulting crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-c4b9c4459bc043088ce8a853885cb44b
Source dataset
uspto-grants-1989_12
Patent number
US04886810

Reaction notes

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