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-Phenyl-1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1742970Notes

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.[C:23]1([C:29]2[N:30]=[N:31][N:32]([CH:34]3[CH2:38][CH2:37][NH:36][CH2:35]3)[CH:33]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[N+](=C1CCCCCCCCCC1C1CCCCCCCCCC1)=[N-]>N1C=CC=CC=1>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:17])[C:10]([F:16])=[C:11]([N:36]4[CH2:37][CH2:38][CH:34]([N:32]5[CH:33]=[C:29]([C:23]6[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=6)[N:30]=[N:31]5)[CH2:35]4)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1-cyclopropyl-6,7,8-trifluoro-5-methyl-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (100 mg, 0.37mmol),3-(4-phenyl-1,2,3-triazol-1-yl)pyrrolidine hydrochloride (160 mg, 0.67 mmol) and diazobicycloundecane (102 mg, 0.67 mmol) in (5 ml) pyridine was heated at 90° C. for 24 hrs. The reaction mixture was concentrated and diluted with water. The separated solid was filtered and washed with water followed by ether and was crystallized from methanol. Yield: 89 mg (55%), m.p. 221.4° C. 1H NMR (TFA) δ: 1.20-1.70 (m, 4H), 2.76-3.80 (m, 2H), 4.20-4.96 (m, 5H), 5.74-5.90 (m, 1H), 7.52 (dd, 5H), 8.70 (s, 1H), 9.27 (s, 1H).

Workup

concentrationThe reaction mixture was concentrated
additiondiluted with water
filtrationThe separated solid was filtered
washwashed with water
customwas crystallized from methanol

Sources & evidence

ORD record: ord-9aaf35cd62c84caa8b9984383f0b22b2
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05342846

Reaction notes

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