Chlorotrimethylsilane → HCID 87333265, compound

HRID 1163363Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][NH:20][C:21]([NH2:23])=[S:22])[O:16][C:15]2=[O:24])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.Cl[C:26]1[N:35]=[C:34]2[C:29]([C:30](=[O:42])[C:31]([C:39]([OH:41])=[O:40])=[CH:32][N:33]2[CH:36]2[CH2:38][CH2:37]2)=[CH:28][C:27]=1[F:43].C[Si](C)(C)Cl.C(N(CC)CC)C>C(#N)C.O>[CH:36]1([N:33]2[C:34]3[C:29](=[CH:28][C:27]([F:43])=[CH:26][N:35]=3)[C:30](=[O:42])[C:31]([C:39]([OH:41])=[O:40])=[C:32]2[N:11]2[CH2:12][CH2:13][N:8]([C:7]3[CH:6]=[CH:5][C:4]([N:14]4[CH2:18][C@H:17]([CH2:19][NH:20][C:21]([NH2:23])=[S:22])[O:16][C:15]4=[O:24])=[CH:3][C:2]=3[F:1])[CH2:9][CH2:10]2)[CH2:37][CH2:38]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 100 mg [(5S)-3-(3-fluoro-4-piperazin-1-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-thiourea (0.28 mmol), 87.98 mg 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (0.31 mmol), 71.57 μl trimethylchlorosilane (0.56 mmol) and 118.31 μl triethylamine (1.4 mmol) in acetonitrile was stirred in a micro wave oven for 8 min at 150° C. The reaction mixture was diluted with water and the solid filtered. The solid was purified by chromatography using a 95/5 dichloromethane/methanol mixture with 1% acetic acid as eluent to leave 50 mg of an oily residue which was crystallized from a ETOAC/hexane mixture.

Workup

filtrationthe solid filtered
customThe solid was purified by chromatography

Sources & evidence

ORD record: ord-7677f4b222f54be88692b3c67bb831af
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820823B2

Reaction notes

Loading…