Chlorotrimethylsilane → HCID 86597770, compound

HRID 1163361Notes

Reaction equation

HRID 1163361 reaction equation
C[S:2][C:3](=[S:25])[NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[C:14]([F:24])[CH:13]=2)[CH2:7]1.Cl[C:27]1[N:36]=[C:35]2[C:30]([C:31](=[O:43])[C:32]([C:40]([OH:42])=[O:41])=[CH:33][N:34]2[CH:37]2[CH2:39][CH2:38]2)=[CH:29][C:28]=1[F:44].[CH3:45][Si](C)(C)Cl>C(#N)C>[CH:37]1([N:34]2[C:35]3[C:30](=[CH:29][C:28]([F:44])=[C:27]([N:21]4[CH2:20][CH2:19][N:18]([C:15]5[CH:16]=[CH:17][C:12]([N:8]6[CH2:7][C@@H:6]([CH:5]([CH3:45])[NH:4][C:3]([SH:2])=[S:25])[O:10][C:9]6=[O:11])=[CH:13][C:14]=5[F:24])[CH2:23][CH2:22]4)[N:36]=3)[C:31](=[O:43])[C:32]([C:40]([OH:42])=[O:41])=[CH:33]2)[CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 110551427-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 86597768HCID 86597768, compound

Product 1

HCID 86597770HCID 86597770, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 100 mg [(5S)-3-(3-fluoro-4-piperazin-1-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-dithiocarbamic acid methyl ester (0.26 mmol), 73.51 mg 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (0.26 mmol) 108 μl triethylamine (0.78 mmol) and 65 μl trimethyl-chlorsilane (0.52 mmol), in acetonitrile was stirred in a micro wave oven for 8 min at 150° C. The solution was decanted from sticky solid, evaporated and the residue digested in water. The solid was filtered and the purified by chromatography using a 9/1 dichloromethane/methanol mixture with 1% acetic acid.

Workup

  1. customThe solution was decanted from sticky solid
  2. customevaporated
  3. filtrationThe solid was filtered
  4. customthe purified by chromatography

Sources & evidence

ORD record
ord-01d6367137c24fe7bd3f8e63ced7f47e
Source dataset
uspto-grants-2010_10
Patent number
US07820823B2

Reaction notes

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