Triethylamine → N-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-7-chloro-N-methylthieno[3,2-b]pyridine-2-carboxamide

HRID 1825104Notes

Reaction equation

HRID 1825104 reaction equation
ClC1C=CN=C2C=C(C(N(CCO)C)=O)SC=12.[Si](Cl)(C(C)(C)C)(C)C.CCN(CC)CC.[Cl:33][C:34]1[CH:39]=[CH:38][N:37]=[C:36]2[CH:40]=[C:41]([C:43]([N:45]3[CH2:49]CC[C@H:46]3[CH2:50][O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53])=[O:44])[S:42][C:35]=12>>[Si:52]([O:51][CH2:50][CH2:46][N:45]([CH3:49])[C:43]([C:41]1[S:42][C:35]2[C:36](=[N:37][CH:38]=[CH:39][C:34]=2[Cl:33])[CH:40]=1)=[O:44])([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 207677677-chloro-2-[(S)-2-([t-butyldimethylsilyloxy]methyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridineHCID 22143489HCID 22143489, compound

Product 1

HCID 22143612N-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-7-chloro-N-methylthieno[3,2-b]pyridine-2-carboxamideYield 78%

Procedure

This material was prepared from 7-chloro-N-(2-hydroxyethyl)-N-methylthieno[3,2-b]pyridine-2-carboxamide 31a (1.27 g, 4.68 mmole), t-butyldimethylsilyl chloride (0.705 g, 4.68 mmole) and Et3N (0.718 ml, 4.68 mmole) in a manner as previously described for 3b to give an orange oil (1.40 g, 78%). 1H NMR (300 MHz, CDCl3) ε 8.61 (1H, d, J=5.1 Hz), 7.74 (1H, s), 7.32 (1H, d, J=5.1 Hz), 3.89 (2H, m), 3.71 (2H, m), 3.37 (3H, s), 0.89 (9H, m), 0.07 (6H, m); ESIMS (MH+): 385.10.

Sources & evidence

ORD record
ord-945765921d7642b8b7d21b85be0215b4
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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