Chlorotrimethylsilane → HCID 67278842, compound

HRID 1893864Notes

Reaction equation

HRID 1893864 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[CH2:20]([O:27][C:28](=[O:60])[CH2:29][CH2:30][C:31]([O:33][C:34]1([CH2:40][O:41][C:42]2[CH:47]=[CH:46][C:45]([N:48]3[CH2:52][C@H:51]([CH2:53][NH:54][C:55](=[O:57])[CH3:56])[O:50][C:49]3=[O:58])=[CH:44][C:43]=2[F:59])[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)=[O:32])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C.C[Si](C)(C)Cl>CN1CCCC1=O>[CH2:20]([O:27][C:28](=[O:60])[CH2:29][CH2:30][C:31]([O:33][C:34]1([CH2:40][O:41][C:42]2[CH:47]=[CH:46][C:45]([N:48]3[CH2:52][C@H:51]([CH2:53][NH:54][C:55](=[O:57])[CH3:56])[O:50][C:49]3=[O:58])=[CH:44][C:43]=2[F:59])[CH2:39][CH2:38][N:37]([C:2]2[C:3]([F:19])=[CH:4][C:5]3[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]([CH:12]4[CH2:14][CH2:13]4)[C:10]=3[N:11]=2)[CH2:36][CH2:35]1)=[O:32])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 110551427-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 67279585HCID 67279585, compound

Product 1

HCID 67278842HCID 67278842, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In analogy to example 72 step 7, with 113 mg 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-[1,8]naphthyridine-3-carboxylic acid (MW: 282.66, 0.4 mmol), 230 mg succinic acid 4-{4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-piperidin-4-yl ester benzyl ester (MW: 571.60, 0.4 mmol), 161 mg triethylamine (MW: 101.19, 1.6 mmol) and 87 mg trimethylchlorsilan (MW: 108.64, 0.8 mmol) in 2 ml N-methyl-pyrrolidin-2-one. Yield: 25 mg, 7.6%. MS: 819 (M+H)+, 817.8, Method ESI+, ESI−.

Sources & evidence

ORD record
ord-21245dff855f448e8af13f1d9c0b36aa
Source dataset
uspto-grants-2013_08
Patent number
US08513231B2

Reaction notes

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