Chlorotrimethylsilane → HCID 69121517, compound

HRID 2387569Notes

Reaction equation

[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH2:16][C@H:15]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:14][C:13]3=[O:22])=[CH:8][C:7]=2[F:23])[CH2:2]1.Cl[C:25]1[N:34]=[C:33]2[C:28]([C:29](=[O:41])[C:30]([C:38]([OH:40])=[O:39])=[CH:31][N:32]2[CH:35]2[CH2:37][CH2:36]2)=[CH:27][C:26]=1[F:42].C[Si](C)(C)Cl.C(N(CC)CC)C>CN1CCCC1=O>[C:19]([NH:18][CH2:17][CH:15]1[O:14][C:13](=[O:22])[N:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH:3]3[CH2:4][N:1]([C:25]4[N:34]=[C:33]5[C:28]([C:29](=[O:41])[C:30]([C:38]([OH:40])=[O:39])=[CH:31][N:32]5[CH:35]5[CH2:37][CH2:36]5)=[CH:27][C:26]=4[F:42])[CH2:2]3)=[C:7]([F:23])[CH:8]=2)[CH2:16]1)(=[O:21])[CH3:20]

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 100 mg N-{(5S)-3-[4-(Azetidin-3-yloxy)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-yl methyl}-acetamide (MW: 323.32, 0.31 mmol), 73 mg 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-Naphthyridine-3-carboxylic acid (MW: 282.66, 0.25 mmol), 0.066 ml trimethylchlorosilane (MW: 108.64, d=0.859, 0.51 mmol) and 0.108 ml triethylamine (MW: 101.19, d=0.726, 0.77 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: 55 mg, 30%. MS: 570.5 (M+H)+, Method ESI+. Molecular Weight=570

Workup

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

Sources & evidence

ORD record: ord-25f7be45a0e5405895ea3b647ac1192b
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268812B2

Reaction notes

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