5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 19005970, compound

HRID 1742965Notes

Reaction equation

[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.Cl.Cl.[NH2:24][C:25]1[N:26]=[N:27][N:28]([CH:30]2[CH2:34][CH2:33][NH:32][CH2:31]2)[CH:29]=1.N1(C2CCCCCCCCCC2)CCCCCCCCCN1>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:32]2[CH2:33][CH2:34][CH:30]([N:28]3[CH:29]=[C:25]([NH2:24])[N:26]=[N:27]3)[CH2:31]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (100 mg, 0.67 mmol), 3-(4-amino-1,2,3-triazol-1-yl)pyrrolidine dihydrochloride (185 mg, 0.83 mmol) and diazabicycloundecane (127 mg, 0.83 mmol) in pyridine (3 ml) was heated at 110° C. for 24 hrs. Reaction mixture was concentrated to dryness under vacuum and residue was dissolved in water, extracted with methylene chloride, dried over sodium sulfate and concentrated to dryness. The solid residue thus obtained was crystallized from chloroform to brown solid. Yield 15 mg (10.4%), m.p. 210°-213° C. 1H NMR (TFA) δ: 1.22-1.58 (m, 4H), 2.70-2.90 (m, 2H), 4.06-4.54 (m, 5H), 5.48-5.60 (m, 1H), 7.79 (s, 1H), 9.14 (s, 1H).

Workup

customReaction mixture
concentrationwas concentrated to dryness under vacuum and residue
dissolutionwas dissolved in water
extractionextracted with methylene chloride
dry with materialdried over sodium sulfate
concentrationconcentrated to dryness
customThe solid residue thus obtained
customwas crystallized from chloroform to brown solid

Sources & evidence

ORD record: ord-070d1e6bd67f481c8ebd872ac55b8ecd
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05342846

Reaction notes

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