1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 70395691, compound

HRID 477021Notes

Reaction equation

HRID 477021 reaction equation
N[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.N[C@H:23]1[C@H:27]([CH3:28])CNC1.C1CCN2C(=NCCC2)CC1>C(#N)C>[CH:15]1([N:7]2[C:8]3[C:3](=[CH:2][C:11]([F:12])=[CH:10][C:9]=3[F:14])[C:4](=[O:21])[CH:5]=[CH:6]2)[CH2:17][CH2:16]1.[CH:28]1([C:5]2([C:18]([OH:20])=[O:19])[C:4](=[O:21])[C:3]3[C:8](=[C:9]([F:14])[CH:10]=[C:11]([F:12])[CH:2]=3)[NH:7][CH2:6]2)[CH2:27][CH2:23]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10329256rel-(3R,4S)-4-Methyl-3-pyrrolidinamineHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 70395691HCID 70395691, compoundYield 85.5%

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 (1.5 g), trans-3-amino-4-methylpyrrolidine (0.76 g), DBU (0.77 g), and acetonitrile (30 ml) was refluxed for 7 hours. The precipitated crystals were collected by filtration after cooling, washed with acetonitrile, and dried. Recrystallization from chloroform-ethanol gave cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.05 g), m.p. 234°-236° C.

Workup

  1. temperaturewas refluxed for 7 hours
  2. filtrationThe precipitated crystals were collected by filtration
  3. temperatureafter cooling
  4. washwashed with acetonitrile
  5. customdried
  6. customRecrystallization from chloroform-ethanol

Sources & evidence

ORD record
ord-45284f54a4a64931bd856d65207ebc86
Source dataset
uspto-grants-1989_12
Patent number
US04886810

Reaction notes

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