1-Cyclopropyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid → 1-Cyclopropyl-6,8-difluoro-5-methyl-7-[3-(4-methyl-1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

HRID 1742946Notes

Reaction equation

HRID 1742946 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.Cl.[CH3:23][C:24]1[N:25]=[N:26][N:27]([CH:29]2[CH2:33][CH2:32][NH:31][CH2:30]2)[CH:28]=1.N1(C2CCCCCCCCCC2)CCCCCCCCCN1>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:17])[C:10]([F:16])=[C:11]([N:31]4[CH2:32][CH2:33][CH:29]([N:27]5[CH:28]=[C:24]([CH3:23])[N:25]=[N:26]5)[CH2:30]4)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 146512581-Cyclopropyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 190059493-(4-Methyl-1,2,3-triazol-1-yl)pyrrolidine hydrochlorideHCID 57346892Diazabicycloundecane

Product 1

HCID 190059311-Cyclopropyl-6,8-difluoro-5-methyl-7-[3-(4-methyl-1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 50 mg (0.168 mmol) of 1-cyclopropyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 3-(4-methyl-1,2,3-triazol -1-yl)pyrrolidine hydrochloride (79 mg, 0.421 mmol) and 64 mg (0.421 mmol) of DBU (diazabicyloundecane) in dry acetonitrile (5 ml) was refluxed under nitrogen for 46 h. The yellow solution was concentrated to dryness and the residue was triturated with acetonitrile and thus separated solid was filtered. The supernatant was evaporated to dryness and water was added to the residue and separated solid was collected (30 mg, 43%), m.p. 232°-234° C. 1H NMR (TFA) δ: 9.26 (s, 1H), 8.37 (s, 1H), 5.78-5.58 (m, 1H) 4.85-4.1 (m, 5H), 3.0-2.7 (m, 5H), 2.68 (s, 3H), 1.65-1.15 (m, 4H). Anal. calcd. for C21H21F2N5O3 : C, 58.74; H, 4.93; N, 16.31. Found: C, 58.14; H, 5.06; N, 16.08.

Workup

  1. temperaturewas refluxed under nitrogen for 46 h
  2. concentrationThe yellow solution was concentrated to dryness
  3. customthe residue was triturated with acetonitrile and thus separated solid
  4. filtrationwas filtered
  5. customThe supernatant was evaporated to dryness and water
  6. additionwas added to the residue
  7. customseparated solid
  8. customwas collected (30 mg, 43%), m.p. 232°-234° C

Sources & evidence

ORD record
ord-4f7c31e031514dc1b29fe8fc5dc78cc7
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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