1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19006047, compound

HRID 1742971Notes

Reaction equation

HRID 1742971 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.Cl.[N:22]1[N:23]([CH:27]2[CH2:31][CH2:30][NH:29][CH2:28]2)[N:24]=[N:25][CH:26]=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:29]4[CH2:30][CH2:31][CH:27]([N:23]5[N:24]=[N:25][CH:26]=[N:22]5)[CH2:28]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19005971HCID 19005971, compound

Product 1

HCID 19006047HCID 19006047, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-cyclopropyl-6,7,8-trifluoro-1, 4-dihydro-4-oxo-quinoline-3-carboxylic acid (28.3 mg, 0.1 mmol), 3-(1,2,3,4-tetrazol-2-yl) pyrrolidine hydrochloride (35.1 mg, 0.2 mmol) and DBU (45.6 mg, 0.3 mmol) in acetonitrile (2 ml) was refluxed under nitrogen for 23 hrs. The solvent was then evaporated to dryness. The residue was diluted with water and extracted with chloroform. The organic extract was dried over Na2SO4, concentrated and the residue was crystallized from methanol-water. Yield: 12 mg, m.p. 192°-199° C. 1H NMR (CDCl3) δ: 8.7 (s, 1H), 8.5 (s, 1H), 7.8 (dd, 1H), 5.6-5.4 (m, 1H), 4.46-3.76 (m, 5H), 2.9-2.45 (m, 2H), 1.35-1.02 (m, 4H).

Workup

  1. customThe solvent was then evaporated to dryness
  2. additionThe residue was diluted with water
  3. extractionextracted with chloroform
  4. extractionThe organic extract
  5. dry with materialwas dried over Na2SO4
  6. concentrationconcentrated
  7. customthe residue was crystallized from methanol-water

Sources & evidence

ORD record
ord-148c075a1d9f4e748c3e3ba379649d0b
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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