1,8-Diazabicyclo(5.4.0)undec-7-ene → (-)-9-Fluoro-3(S)-methyl-10-[3-(4-methyl-1,2,3-triazol-1-yl)pyrrolidin-1-yl]-7-oxo-2,3-dihydro-7H-pyrido-[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid

HRID 1742963Notes

Reaction equation

HRID 1742963 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.[CH3:22][C:23]1[N:24]=[N:25][N:26]([CH:28]2[CH2:32][CH2:31][NH:30][CH2:29]2)[CH:27]=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[F:1][C:2]1[C:3]([N:30]2[CH2:31][CH2:32][CH:28]([N:26]3[CH:27]=[C:23]([CH3:22])[N:24]=[N:25]3)[CH2:29]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 190059493-(4-Methyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride

Product 1

HCID 18654492(-)-9-Fluoro-3(S)-methyl-10-[3-(4-methyl-1,2,3-triazol-1-yl)pyrrolidin-1-yl]-7-oxo-2,3-dihydro-7H-pyrido-[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution 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 141 mg (0.75 mmol) of 3-(4-methyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride in 3 ml of acetonitrile in the presence of 152.24 mg (1 mmol) of DBU was refluxed for 3 days under nitrogen atmosphere. The suspension was then evaporated and water was added to the residue and solid collected and washed with methanol to yield after drying 50 mg of the desired product, m.p. 241°-242° C. 1H NMR (TFA) δ: 9.16 (s, 1H), 8.37 (s, 1H), 7.99 (d, 13.3Hz, 1H), 5.75-5.6 (m, 1H), 5.15-4.1 (m, 7H), 3-2.6 (m, 2H), 2.67 (s , 3H), 1.8 (d, 6.8Hz, 3H). Anal. calcd. for C20H20FN5O4 . 1/2 H2O: C, 56.87; H, 5.01; N, 16.58. Found: C, 57.30; H, 4.77; N, 16.75.

Workup

  1. customThe suspension was then evaporated
  2. additionwater was added to the residue and solid
  3. customcollected
  4. washwashed with methanol
  5. customto yield
  6. dry with materialafter drying 50 mg of the desired product, m.p. 241°-242° C

Sources & evidence

ORD record
ord-e0a4a5056b5e4f118ceb9e8471a967c4
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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