1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19006026, compound

HRID 1742972Notes

Reaction equation

HRID 1742972 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.[N:21]1([CH:26]2[CH2:31][CH2:30][CH2:29][N:28](Cl)[CH2:27]2)[CH:25]=[CH:24][N:23]=[N:22]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:28]4[CH2:29][CH2:30][CH2:31][CH:26]([N:21]5[CH:25]=[CH:24][N:23]=[N:22]5)[CH2:27]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 86748097HCID 86748097, compound

Product 1

HCID 19006026HCID 19006026, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (50 mg, 0.18 mmol) and 3-(1,2,3-triazol-1-yl)piperidine-1-yl hydrochloride (83 mg, 0.44 mmol) in 3 ml of acetonitrile was added 67 mg (0.44 mmol) of DBU. The solution was heated at reflux under nitrogen for 16 hrs. The suspension was cooled and the solid collected, washed with water, dried to yield 50 mg of the title product, m.p. 239°-240° C. 1H NMR (TFA) δ: 9.35 (s, 1H), 8.61 (s, 1H), 8.51 (s, 1H), 8.16 (d, J=10.6Hz, 1H), 5.45-5.15 (m, 1H), 4.7-3.55 (m, 5H), 2.85-2.05 (m, 4H), 1.8-1.3 (m, 4H).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux under nitrogen for 16 hrs
  3. temperatureThe suspension was cooled
  4. customthe solid collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-7a41607280464ae2ba2e942313447f6e
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

Loading…