Chlorotrimethylsilane → HCID 69121786, compound

HRID 2387570Notes

Reaction equation

[NH:1]1[CH2:4][CH:3]([CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][C:14]3=[O:23])=[CH:9][C:8]=2[F:24])[CH2:2]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>CN1CCCC1=O>[C:20]([NH:19][CH2:18][CH:16]1[O:15][C:14](=[O:23])[N:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH:3]3[CH2:4][N:1]([C:26]4[N:35]=[C:34]5[C:29]([C:30](=[O:42])[C:31]([C:39]([OH:41])=[O:40])=[CH:32][N:33]5[CH:36]5[CH2:38][CH2:37]5)=[CH:28][C:27]=4[F:43])[CH2:2]3)=[C:8]([F:24])[CH:9]=2)[CH2:17]1)(=[O:22])[CH3:21]

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 179 mg N-{(5S)-3-[4-(Azetidin-3-ylmethoxy)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-yl methyl}-acetamide (MW: 337.35, 0.31 mmol), 100 mg 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-Naphthyridine-3-carboxylic acid (MW: 282.66, 0.25 mmol), 0.134 ml trimethylchlorosilane (MW: 108.64, d=0.859, 1.059 mmol) and 0.197 ml triethylamine (MW: 101.19, d=0.726, 1.41 mmol) in 2 ml N-methyl-pyrrolidin-2-one was heated under stirring in a micro wave oven at 150° C. for 7 min. The N-methyl-pyrrolidin-2-one was evaporated, the residue was purified by chromatography. Yield: 82 mg, 40%. MS: 583.5 (M+H)+, Method ESI+. Molecular Weight=584

Workup

temperaturewas heated
customThe N-methyl-pyrrolidin-2-one was evaporated
customthe residue was purified by chromatography

Sources & evidence

ORD record: ord-c9efae6ce65e4745b5bf75c0e9aba5ac
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268812B2

Reaction notes

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