Triethylamine → 5-Amino-7-(2-acetylaminomethylmorpholino)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 728772Notes

Reaction equation

HRID 728772 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.[C:22]([NH:25][CH2:26][CH:27]1[O:32][CH2:31][CH2:30][NH:29][CH2:28]1)(=[O:24])[CH3:23].C(N(CC)CC)C>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:29]2[CH2:30][CH2:31][O:32][CH:27]([CH2:26][NH:25][C:22](=[O:24])[CH3:23])[CH2:28]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

5

Reactant 3

HCID 8471TriethylamineHCID 10241064N-(morpholin-2-ylmethyl)acetamideHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 541975265-Amino-7-(2-acetylaminomethylmorpholino)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 49.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1 g of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 1.15 g of 2-acetylaminomethylmorpholine, 1 g of triethylamine and10 ml of pyridine was heated under reflux for 16 hours. The reaction mixture was concentrated to dryness under reduced pressure, and ethyl acetate was added to the residue. The resulting crystals were collected byfiltration, and suspended in 20 ml of water. The suspension was extracted with chloroform, and the extract was dried and concentrated. Recrystallization of the residue from ethanol gave 720 mg of 5-amino-7-(2-acetylaminomethylmorpholino)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. m.p. 228°-229° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure, and ethyl acetate
  4. additionwas added to the residue
  5. filtrationThe resulting crystals were collected byfiltration
  6. extractionThe suspension was extracted with chloroform
  7. customthe extract was dried
  8. concentrationconcentrated
  9. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-130de1b2fcd94e0f87161ed9347fbd4a
Source dataset
uspto-grants-1991_09
Patent number
US05051419

Reaction notes

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