1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Amino-7-(3-amino-3-methyl1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro4-oxoquinoline-3-carboxylic acid

HRID 477020Notes

Reaction equation

HRID 477020 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][C:23]1([CH3:28])[CH2:27][CH2:26][NH:25][CH2:24]1.C1CCN2C(=NCCC2)CC1>C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:25]2[CH2:26][CH2:27][C:23]([NH2:22])([CH3:28])[CH2:24]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[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 155958533-Methylpyrrolidin-3-amine

Product 1

HCID 157293795-Amino-7-(3-amino-3-methyl1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro4-oxoquinoline-3-carboxylic acidYield 60.4%

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), 3-amino-3-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, and washed with acetonitrile. The crystals were suspended in water (50 ml) and dissolved by addition of a 10% aqueous solution of acetic acid. The solution was treated with activated carbon, and adjusted to pH 7-8 with 10% aqueous ammonia. The precipitated crystals were collected by filtration, washed with water and then with ethanol, and dried to give 5-amino-7-(3-amino-3-methyl1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro4-oxoquinoline-3-carboxylic acid (1.15 g), m.p. 271°-273° C. (decomp.).

Workup

  1. temperaturewas refluxed for 7 hours
  2. filtrationThe precipitated crystals were collected by filtration
  3. temperatureafter cooling
  4. washwashed with acetonitrile
  5. dissolutiondissolved by addition of a 10% aqueous solution of acetic acid
  6. additionThe solution was treated with activated carbon
  7. filtrationThe precipitated crystals were collected by filtration
  8. washwashed with water
  9. dry with materialwith ethanol, and dried

Sources & evidence

ORD record
ord-2acbf4ed0ca046c9971338733affc3b8
Source dataset
uspto-grants-1989_12
Patent number
US04886810

Reaction notes

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