Ciprofloxacin → HCID 71565880, compound

HRID 1525122Notes

Reaction equation

[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:14]4[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.CS(O[CH2:30][C@@H:31]1[O:35][C:34](=[O:36])[N:33]([C:37]2[CH:38]=[CH:39][C:40]3[S:41][CH2:42][C:43](=[O:47])[NH:44][C:45]=3[N:46]=2)[CH2:32]1)(=O)=O>>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH2:30][C@H:31]5[O:35][C:34](=[O:36])[N:33]([C:37]6[CH:38]=[CH:39][C:40]7[S:41][CH2:42][C:43](=[O:47])[NH:44][C:45]=7[N:46]=6)[CH2:32]5)[CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:2][CH2:3]1

Participants

Reactant 2

HCID 2764Ciprofloxacin

HCID 87281425HCID 87281425, compound

Product 1

HCID 71565880HCID 71565880, compound

Procedure

In analogy to Example 1, starting from 1-cyclopropyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxo-3-quinoline carboxylic acid (commercial; 166 mg) and 6-[(5R)-5-[[(methylsulfonyl)oxy]methyl]-2-oxo-3-oxazolidinyl]-2H-pyrido[3,2-b]-1,4-thiazin-3(4H)-one (prepared in analogy to its (S) enantiomer described in WO 2010/041194; 180 mg), the title compound was obtained as a beige solid after CC (DCM/MeOH 9:1) and crystallization from EtOH.

Sources & evidence

ORD record: ord-e46f254fdf744ea9bf44735037e40231
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079922B2

Reaction notes

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