1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19006034, compound

HRID 1742982Notes

Reaction equation

HRID 1742982 reaction equation
Cl.[CH3:2][C:3]1[N:7]([CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)[N:6]=[N:5][CH:4]=1.C1CCN2C(=NCCC2)CC1.[CH:24]1([N:27]2[C:36]3[C:31](=[CH:32][C:33]([F:40])=[C:34](F)[C:35]=3[O:37][CH3:38])[C:30](=[O:41])[C:29]([C:42]([OH:44])=[O:43])=[CH:28]2)[CH2:26][CH2:25]1>C(#N)C>[CH:24]1([N:27]2[C:36]3[C:31](=[CH:32][C:33]([F:40])=[C:34]([N:10]4[CH2:11][CH2:12][CH:8]([N:7]5[C:3]([CH3:2])=[CH:4][N:5]=[N:6]5)[CH2:9]4)[C:35]=3[O:37][CH3:38])[C:30](=[O:41])[C:29]([C:42]([OH:44])=[O:43])=[CH:28]2)[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 70194651-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acidHCID 19005975HCID 19005975, compound

Product 1

HCID 19006034HCID 19006034, compoundYield 6.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(5-methyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride (64 mg, 0.34 mmol) and DBU (77 mg, 0.51 mmol) was added to a suspension of 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (50 mg, 0.17 mmol) in acetonitrile (5 ml). The reaction mixture was refluxed for 18 hrs and then concentrated to dryness. The residue was triturated with water and thus separated solid was filtered, washed with water, acetonitrile and dried to give 5 mg of title product. m.p. 226°-228° C.; 1H NMR (TFA) δ: 9.35 (s, 1H), 8.32 (s, 1H), 8.08 (d, 1H), 5.72 (m, 1H), 4.30-4.80 (m, 4H), 4.10 (m, 1H), 3.80 (s, 3H), 2.90 (m, 2H), 2.72 (s, 3H), 1.12-1.64 (m, 4H).

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hrs
  2. concentrationconcentrated to dryness
  3. customThe residue was triturated with water and thus separated solid
  4. filtrationwas filtered
  5. washwashed with water, acetonitrile
  6. customdried

Sources & evidence

ORD record
ord-1dda856b6470416ebbbb0681a411e91c
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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