Potassium Iodide → HCID 13365560, compound

HRID 1710185Notes

Reaction equation

F[C:2]1[C:20](F)=[C:19](F)[C:18](F)=CC=1C(C(C(OCC)=O)C(OCC)=O)=O.[CH:24]1([N:27]2[C:36]3[C:31](=[CH:32][C:33]([F:44])=[C:34]([N:38]4[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]4)[C:35]=3[F:37])[C:30](=[O:45])[C:29]([C:46]([OH:48])=[O:47])=[CH:28]2)[CH2:26][CH2:25]1.C1(CCl)CC1.[I-].[K+]>C(N(CC)CC)C>[CH:24]1([N:27]2[C:36]3[C:31](=[CH:32][C:33]([F:44])=[C:34]([N:38]4[CH2:39][CH2:40][N:41]([CH2:18][CH:19]5[CH2:2][CH2:20]5)[CH2:42][CH2:43]4)[C:35]=3[F:37])[C:30](=[O:45])[C:29]([C:46]([OH:48])=[O:47])=[CH:28]2)[CH2:25][CH2:26]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3 5 g (0.01 mol) of 1-cyclopropyl-6,8-difluoro-7-(piperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 2.1 g of triethylamine, 1.8 g of cyclopropylmethyl chloride and 3.3 g of potassium iodide is heated to 80° C. for 6 hours. Thereafter, the mixture is evaporated down in vacuo, 30 ml of water are added, the mixture is adjusted to pH 5 and the precipitate is filtered off under suction, washed with water and methanol and recrystallised from glycol monomethyl ether. 1.8 g of 1-cyclopropyl-7-(4-cyclopropylmethylpiperazin-1-yl)-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid having a decomposition temperature of 246°-248° C. are obtained.

Workup

customThereafter, the mixture is evaporated down in vacuo, 30 ml of water
additionare added
filtrationthe precipitate is filtered off under suction
washwashed with water and methanol
customrecrystallised from glycol monomethyl ether

Sources & evidence

ORD record: ord-d1c79b1491354fb49495cd68ee634fa2
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04952695

Reaction notes

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