1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 53860290, compound

HRID 1742964

Reaction equation

HRID 1742964 reaction equation
[F:1][C:2]1[C:3](F)=[C:4]2[O:9][CH2:8][C@H:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([OH:19])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23.Cl.[N:22]1([CH:27]2[CH2:31][CH2:30][NH:29][CH2:28]2)[CH:26]=[N:25][CH:24]=[N:23]1.C1CCN2C(=NCCC2)CC1>C(#N)C>[F:1][C:2]1[C:3]([N:29]2[CH2:30][CH2:31][CH:27]([N:22]3[CH:26]=[N:25][CH:24]=[N:23]3)[CH2:28]2)=[C:4]2[O:9][CH2:8][C@H:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([OH:19])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 688333Levofloxacin q-acidHCID 190059941-(pyrrolidin-3-yl)-1H-1,2,4-triazole hydrochloride

Product 1

HCID 53860290HCID 53860290, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 70.25 mg (0.25 mmol) of (-) -9,10-difluoro-3(S)-methyl-7-oxo-2,3-dihydro-7H-pyrido [1,2,3-de]-1,4-benzoxazine-6-carboxylic acid and 87 mg (0.5 mmol) of 3-(1,2,4-triazol-1-yl)pyrrolidine hydrochloride in 3 ml of acetonitrile in the presence of 76 mg (0.5 mmol) DBU was stirred under nitrogen at reflux condition overnight. The yellow solution was then evaporated to dryness and to the residue, water was added and solid collected. The off-white solid was dissolved in chloroform and the small amounts of the suspension were filtered off. The supernatant was evaporated and to the residue, water was added and solid collected (60 mg), m.p. 229°-231° C. 1H NMR (CDCl3) δ: 8.59 (s, 1H), 8.26 (s, 1H), 7.98 (s, 1H), 7.7 (d, 13.5Hz, 1H), 5.17-5.00 (m, 1H), 4.6-3.73 (m, 7H), 2.67-2.4 (m, 2H), 1.61 (d, 6.7Hz, 3H).

Workup

  1. temperatureat reflux condition overnight
  2. customThe yellow solution was then evaporated to dryness and to the residue, water
  3. additionwas added
  4. customsolid collected
  5. dissolutionThe off-white solid was dissolved in chloroform
  6. filtrationthe small amounts of the suspension were filtered off
  7. customThe supernatant was evaporated and to the residue, water
  8. additionwas added
  9. customsolid collected (60 mg), m.p. 229°-231° C

Sources & evidence

ORD record
ord-6bc681907c20481e894d9c29497a675a
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Linked notes

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