1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19005947, compound

HRID 1742973Notes

Reaction equation

HRID 1742973 reaction equation
Cl.[N:2]1([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][N:4]=[N:3]1.C1CCN2C(=NCCC2)CC1.[NH2:24][C:25]1[C:34]([F:35])=[C:33](F)[C:32]([F:37])=[C:31]2[C:26]=1[C:27](=[O:44])[C:28]([C:41]([OH:43])=[O:42])=[CH:29][N:30]2[CH:38]1[CH2:40][CH2:39]1>C(#N)C>[NH2:24][C:25]1[C:34]([F:35])=[C:33]([N:9]2[CH2:10][CH2:11][CH2:12][CH:7]([N:2]3[CH:6]=[CH:5][N:4]=[N:3]3)[CH2:8]2)[C:32]([F:37])=[C:31]2[C:26]=1[C:27](=[O:44])[C:28]([C:41]([OH:43])=[O:42])=[CH:29][N:30]2[CH:38]1[CH2:40][CH2:39]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19005979HCID 19005979, compound

Product 1

HCID 19005947HCID 19005947, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(1,2,3-triazol-1-yl)pyridine hydrochloride (63 mg, 0.33 mmol) and DBU (77 mg, 0.5 mmol) were added to a suspension of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (50 mg, 0.18 mmol) in acetonitrile (5 ml). The reaction mixture was refluxed for 48 hrs and then concentrated under vacuo. The residue was diluted with water and thus separated solid was filtered, washed with water, acetonitrile and dried to give 30 mg of desired product. m.p. 252-254° C.; 1H NMR (TFA) δ: 9.36 (s, 1H), 8.65 (s, 1H), 8.53 (s, 1H), 5.28 (m, 1H), 3.60-4.66 (m, 5H), 2.10-2.58 (m, 4H), 1.32-1.68 (m, 4H).

Workup

  1. temperatureThe reaction mixture was refluxed for 48 hrs
  2. concentrationconcentrated under vacuo
  3. additionThe residue was diluted with water and thus separated solid
  4. filtrationwas filtered
  5. washwashed with water, acetonitrile
  6. customdried

Sources & evidence

ORD record
ord-9e50663f6b7d4c15bd30eebb8af22a9a
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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