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

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	tert-Butyldimethylsilyl chloride	HCID 28928	—
Reactant	7-chloro-2-[(S)-2-([t-butyldimethylsilyloxy]methyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridine	HCID 20767767	—
Reactant	HCID 22143489	HCID 22143489	—
Product	N-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-7-chloro-N-methylthieno[3,2-b]pyridine-2-carboxamide	HCID 22143612	78%

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07045528B2
Source dataset	uspto-grants-2006_05
ORD ID	ord-945765921d7642b8b7d21b85be0215b4
Source note	uspto-grants-2006_05