1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 54100980, compound

HRID 1742983

Reaction equation

HRID 1742983 reaction equation
Cl.[N:2]1([CH:7]2[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][N:4]=[N:3]1.C1CCN2C(=NCCC2)CC1.[F:23][CH2:24][CH2:25][N:26]1[C:35]2[C:30](=[CH:31][C:32]([F:38])=[C:33](F)[C:34]=2[F:36])[C:29](=[O:39])[C:28]([C:40]([OH:42])=[O:41])=[CH:27]1>C(#N)C>[F:38][C:32]1[CH:31]=[C:30]2[C:35](=[C:34]([F:36])[C:33]=1[N:9]1[CH2:10][CH2:11][CH:7]([N:2]3[CH:6]=[CH:5][N:4]=[N:3]3)[CH2:8]1)[N:26]([CH2:25][CH2:24][F:23])[CH:27]=[C:28]([C:40]([OH:42])=[O:41])[C:29]2=[O:39]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 127709081-(2-Fluoroethyl)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 190059431-(pyrrolidin-3-yl)-1H-1,2,3-triazole hydrochloride

Product 1

HCID 54100980HCID 54100980, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(1,2,3-triazol-1-yl)pyrrolidinehydrochloride (87 mg) and DBU (76 mg) were added to a suspension of 1-(2-fluoroethyl)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (72 mg, 0.25 mmol) in acetonitrile (5 ml). The reaction mixture was refluxed for 21 hrs, concentrated and the residue was diluted with water. The separated solid was filtered, washed with water and acetonitrile to give 35 mg of the title product. m.p. 240°-243° C. (dec). 1H NMR (TFA) δ: 9.76 (s, 1H), 9.08 (s, 1H), 8.73 (s, 1H), 8.12 (d, 13.7Hz, 1H), 5.8-5.6 (m, 1H), 5.4-4.1 (m, 9H), 3.0-2.65 (m, 2H). Anal. Calcd. for C18H16F3N5O3 . 1/2 H2O; C, 51.93; H, 4.12; N, 16.32.Found: C, 51.77; H, 3.84; N, 15.6.

Workup

  1. temperatureThe reaction mixture was refluxed for 21 hrs
  2. concentrationconcentrated
  3. additionthe residue was diluted with water
  4. filtrationThe separated solid was filtered
  5. washwashed with water and acetonitrile

Sources & evidence

ORD record
ord-72307f8453a341b0aaf1d1b98e778148
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Linked notes

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