Chlorotrimethylsilane → HCID 86613447, compound

HRID 2279666Notes

Reaction equation

HRID 2279666 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].Cl.[C:21]([NH:24][CH2:25][C@@H:26]1[O:30][C:29](=[O:31])[N:28]([C:32]2[CH:75]=[CH:74][C:35]([O:36][CH2:37][C:38]3([O:44][C:45](=[O:73])[CH:46]([NH:62][C:63]([O:65][CH2:66][C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)=[O:64])[CH2:47][CH2:48][CH2:49][CH2:50][NH:51][C:52]([O:54][CH2:55][C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)=[O:53])[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)=[C:34]([F:76])[CH:33]=2)[CH2:27]1)(=[O:23])[CH3:22].C(N(CC)CC)C.C[Si](C)(C)Cl>CN1CCCC1=O>[C:21]([NH:24][CH2:25][C@@H:26]1[O:30][C:29](=[O:31])[N:28]([C:32]2[CH:75]=[CH:74][C:35]([O:36][CH2:37][C:38]3([O:44][C:45](=[O:73])[CH:46]([NH:62][C:63]([O:65][CH2:66][C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)=[O:64])[CH2:47][CH2:48][CH2:49][CH2:50][NH:51][C:52]([O:54][CH2:55][C:56]4[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=4)=[O:53])[CH2:39][CH2:40][N:41]([C:2]4[N:11]=[C:10]5[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]5[CH:12]5[CH2:14][CH2:13]5)=[CH:4][C:3]=4[F:19])[CH2:42][CH2:43]3)=[C:34]([F:76])[CH:33]=2)[CH2:27]1)(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 110551427-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 67278834HCID 67278834, compound

Product 1

HCID 86613447HCID 86613447, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In analogy to example 1 step 7, with 62 mg 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-[1,8]naphthyridine-3-carboxylic acid (MW: 282.66, 0.25 mmol), 178 mg 2,6-bis-benzyloxycarbonylamino-hexanoic acid 4-{4-[5-(5S)-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-piperidin-4-yl ester hydrochloride (MW: 814.31, 0.22 mmol), 90 mg triethylamine (MW: 101.19, 0.88 mmol) and 48 mg trimethylchlorsilan (MW: 108.64, 0.44 mmol) in 1 ml N-methyl-pyrrolidin-2-one. Yield: 94 mg, 42%. MS: 1025.3 (M+H)+, Method ESI+.

Sources & evidence

ORD record
ord-9ad43107db9f461497157ea7e0bd3592
Source dataset
uspto-grants-2015_09
Patent number
US09133213B2

Reaction notes

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