1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 70283859, compound

HRID 1742962Notes

Reaction equation

HRID 1742962 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]=[CH:25][N: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]=[CH:25][N: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 190059431-(pyrrolidin-3-yl)-1H-1,2,3-triazole hydrochloride

Product 1

HCID 70283859HCID 70283859, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 76 mg (0.27 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 118 mg (0.675 mmol) of 3-(1,2,3-triazol-1-yl) pyrrolidine hydrochloride in 10 ml of dry acetonitrile was added 121 mg (0.81 mmol) of DBU. The reddish brown solution was refluxed for 31 hr. The solvent was then removed under reduced pressure. To the residue water was added and extracted with chloroform. The organic layer was then evaporated to dryness, and to the residue, water was added and solid collected to yield 10 mg of the desired product, m.p. 225°-229° C. 1H NMR (TFA) δ: 9.17 (s, 1H), 8.67 (s, 1H), 8.57 (s, 1H), 7.99 (d, 13.3Hz, 1H), 5.9-5.18 (m, 1H), 5.22-4.07 (m, 7H), 3.13-2.63 (m, 2H), 1.82 (s, 3H), 1.79 (s, 3H). Anal. calcd. for C19H18N5O4F . 1/2 H2O: C, 55.86; H, 4.69; N, 17.16. Found: C, 55.93; H, 4.59; N, 16.37.

Workup

  1. temperatureThe reddish brown solution was refluxed for 31 hr
  2. customThe solvent was then removed under reduced pressure
  3. additionTo the residue water was added
  4. extractionextracted with chloroform
  5. customThe organic layer was then evaporated to dryness
  6. additionto the residue, water was added
  7. customsolid collected

Sources & evidence

ORD record
ord-e2f2508567154e7e8b9bfdbae4d932bc
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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