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

HRID 1742968Notes

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]1([C:28]2[N:29]=[N:30][N:31]([CH:33]3[CH2:37][CH2:36][NH:35][CH2:34]3)[CH:32]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[N+](=C1CCCCCCCCCC1C1CCCCCCCCCC1)=[N-]>N1C=CC=CC=1>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:35]4[CH2:36][CH2:37][CH:33]([N:31]5[CH:32]=[C:28]([C:22]6[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=6)[N:29]=[N:30]5)[CH2:34]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

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (150 mg, 0.53 mmol), 3-(4-phenyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride (252 mg, 1.05 mmol) and diazobicycloundecane (160 mg, 1.05 mmol) in pyridine (5 ml) was heated at 110° C. for 20 hrs, concentrated and diluted with water. The separated solid was filtered, washed with water and crystallized from methanol. Yield: 55 mg (22.3%), m.p. 241.4° C. 1H NMR (TFA) δ: 1.34-1.73 (m, 4H), 2.82-3.09 (m, 2H), 4.20-4.95 (m, 5H), 5.73-5.92 (m, 1H), 7.5-7.92 (m, 4H), 8.15 (d, 1H), 8.80 (s, 1H), 9.30 (s, 1H).

Workup

concentrationconcentrated
additiondiluted with water
filtrationThe separated solid was filtered
washwashed with water
customcrystallized from methanol

Sources & evidence

ORD record: ord-abe82759f54a45f0893d94209b133bed
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05342846

Reaction notes

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