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

HRID 1742967
Notes
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Reaction equation

HRID 1742967 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.Cl.[C:22]([C:25]1[N:26]=[N:27][N:28]([CH:30]2[CH2:34][CH2:33][NH:32][CH2:31]2)[CH:29]=1)([OH:24])=[O:23].[N+](=C1CCCCCCCCCC1C1CCCCCCCCCC1)=[N-]>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:32]4[CH2:33][CH2:34][CH:30]([N:28]5[CH:29]=[C:25]([C:22]([OH:24])=[O:23])[N:26]=[N:27]5)[CH2:31]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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 190059671-(pyrrolidin-3-yl)-1H-1,2,3-triazole-4-carboxylic acid hydrochlorideHCID 22171225Diazobicycloundecane

Product 1

HCID 570442821-Cyclopropyl-6,8-difluoro-7-[3-(4-carboxy-1,2,3-triazol-1-yl]pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

A mixture of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (140 mg, 0.49 mmol), 3-(4-carboxy-1,2,3-triazol-1-yl)pyrrolidine hydrochloride (269 mg, 1.23 mmol) and diazobicycloundecane (187 mg, 1.23 mmol) in acetonitrile (5 ml) was heated at 80°-90° C. for four days. The reaction mixture was concentrated, diluted with water (10 ml) and pH brought down to 4.0 using 1M HCl. The separated solid was filtered and washed with water and crystallized from MeOH/ether to yellow solid. Yield 29 mg (13.2%), m.p. 222°-225° C. 1H NMR (CDCl3 +CD3OD) δ: 1.11-1.42 (m, 4H), 3.88-4.30 (m, 4H), 4.40-4.48 (m, 1H), 5.35-5.55 (m, 1H), 7.8 (d, 1H), 8.41 (s, 1H), 8.79 (s, 1H).

Workup

  1. temperaturewas heated at 80°-90° C. for four days
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water (10 ml)
  4. filtrationThe separated solid was filtered
  5. washwashed with water
  6. customcrystallized from MeOH/ether to yellow solid

Sources & evidence

ORD record
ord-0db786644046470ebd405c2295d4665b
Source dataset
uspto-grants-1994_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05342846

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes