Hydrochloric Acid → HCID 71565878, compound

HRID 1525120Notes

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.I[CH2:26][C@H:27]1[O:31][C:30](=[O:32])[N:29]([C:33]2[CH:34]=[CH:35][C:36]3[S:41][CH2:40][C:39](=[O:42])[NH:38][C:37]=3[CH:43]=2)[CH2:28]1.CCN(C(C)C)C(C)C.Cl>CS(C)=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]([CH2:26][C@H:27]5[O:31][C:30](=[O:32])[N:29]([C:33]6[CH:34]=[CH:35][C:36]7[S:41][CH2:40][C:39](=[O:42])[NH:38][C:37]=7[CH:43]=6)[CH2:28]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

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-cyclopropyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxo-3-quinoline carboxylic acid (commercial; 331 mg), 6-((S)-5-iodomethyl-2-oxooxazolidin-3-yl)-4H-benzo[1,4]thiazin-3-one (prepared according to WO 2008/126034; 395 mg) and DIPEA (0.5 ml) in DMSO (6 ml) was heated at 80° C. for 24 h. The reaction mixture was allowed to reach rt, poured on 0.1N HCl (50 ml) and filtered. The resulting solid was purified by CC (DCM/MeOH 19:1 to 9:1 to 4:1, followed by DCM/MeOH 19:1+1% AcOH), affording after concentration under reduced pressure and subsequent stirring in MeOH/EA a beige solid.

Workup

customto reach rt
filtrationfiltered
customThe resulting solid was purified by CC (DCM/MeOH 19:1 to 9:1 to 4:1, followed by DCM/MeOH 19:1+1% AcOH)
customaffording
concentrationafter concentration under reduced pressure

Sources & evidence

ORD record: ord-f4d11b774a4d41a0ac1894f09033ddce
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079922B2

Reaction notes

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