1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 54550198, compound

HRID 1742975Notes

Reaction equation

Cl.[N:2]1([CH:7]2[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[N:5][CH:4]=[N:3]1.C1CCN2C(=NCCC2)CC1.[CH:24]1([N:27]2[C:36]3[C:31](=[CH:32][C:33]([F:39])=[C:34](F)[C:35]=3[F:37])[C:30](=[O:40])[C:29]([C:41]([OH:43])=[O:42])=[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:39])=[C:34]([N:9]4[CH2:10][CH2:11][CH2:12][CH:7]([N:2]5[CH:6]=[N:5][CH:4]=[N:3]5)[CH2:8]4)[C:35]=3[F:37])[C:30](=[O:40])[C:29]([C:41]([OH:43])=[O:42])=[CH:28]2)[CH2:25][CH2:26]1

Participants

Conditions

Temperature: 90 °C

Procedure

3-(1,2,4-triazol-1-yl)piperidine hydrochloride (300 mg, 1.59 mmol) and DBU (0.48 g, 3.18 mmol) were added to a suspension of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (180 mg, 0.63 mmol) in acetonitrile (15 ml). The reaction mixture was refluxed at 90° C. for 48 hrs and then concentrated under vacuum. The residue was diluted with water and aqueous solution was extracted with chloroform. The organic layer dried over Na2SO4, concentrated and the residue was diluted with water. The separated solid was filtered and washed with 2 ml of acetonitrile. Yield 13 mg, m.p. 217° C.; 1H NMR (TFA) δ: 9.75 (s, 1H), 9.40 (s, 1H), 8.78 (s, 1H), 8.20 (d, 1H), 5.10 (m, 1H), 4.58 (m, 1H), 3.52-4.40 (m, 4H), 2.55 (m, 2H), 2.20 (m, 2H), 1.30-1.70 (m, 4H).

Workup

concentrationconcentrated under vacuum
additionThe residue was diluted with water and aqueous solution
extractionwas extracted with chloroform
dry with materialThe organic layer dried over Na2SO4
concentrationconcentrated
additionthe residue was diluted with water
filtrationThe separated solid was filtered
washwashed with 2 ml of acetonitrile

Sources & evidence

ORD record: ord-45626d59e13749d598e4ebf0e05d0d43
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05342846

Reaction notes

Loading…