1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl 6,8-difluoro-1-(4-fluorophenyl)-7-[3-(1,2,3-triazol-1-yl)-pyrrolidin-1-yl]-1,4-dihydro-4-oxo-quinoline-3-carboxylate

HRID 1742933

Reaction equation

HRID 1742933 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15](F)[C:16]=3[F:18])[C:11](=[O:21])[C:10]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:9]2)=[CH:4][CH:3]=1.Cl.[N:28]1([CH:33]2[CH2:37][CH2:36][NH:35][CH2:34]2)[CH:32]=[CH:31][N:30]=[N:29]1.C1CCN2C(=NCCC2)CC1>C(#N)C>[F:20][C:14]1[CH:13]=[C:12]2[C:17](=[C:16]([F:18])[C:15]=1[N:35]1[CH2:36][CH2:37][CH:33]([N:28]3[CH:32]=[CH:31][N:30]=[N:29]3)[CH2:34]1)[N:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH:9]=[C:10]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:11]2=[O:21]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13728329Ethyl 1-(4-fluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylateHCID 190059431-(pyrrolidin-3-yl)-1H-1,2,3-triazole hydrochloride

Product 1

HCID 15228836Ethyl 6,8-difluoro-1-(4-fluorophenyl)-7-[3-(1,2,3-triazol-1-yl)-pyrrolidin-1-yl]-1,4-dihydro-4-oxo-quinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 1-(4-fluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylate (180 mg, 0.5 mmol), 3-(1,2,3-triazol-1-yl)-pyrrolidine hydrochloride (259 mg, 1.4 mmol) and DBU (384 mg, 2.5 mmol) in acetonitrile (20 ml) was heated at 75° C for 3 h, cooled to r.t. and stirred for another 15 h. The separated solid was filtered, successively washed with acetonitrile and ether. The white crystalline solid thus obtained was dried in vac-oven at 40° C. Yield: 135 mg, 56.7%. 1H NMR (CDCl3) δ: 1.35 (t, 3H), 2.50 (m, 2H), 3.70 (m, 1H), 3.85 (m, 2H), 4.10 (m, 1H), 4.35 (q, 2H), 5.25 (m, 1H), 7.20 (m, 2H), 7.40 (m, 2H), 7.63 (d, 1H), 7.72 (d, 1H), 7.90 (dd, 1H), 8.25 (s, 1H).

Workup

  1. filtrationThe separated solid was filtered
  2. washsuccessively washed with acetonitrile and ether
  3. customThe white crystalline solid thus obtained
  4. customwas dried in vac-oven at 40° C

Sources & evidence

ORD record
ord-11511216a0c94b27830d4f29422fa580
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Linked notes

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