Diisopropylethylamine → 6-Nitro-N-[(3S)-tetrahydro-2H-pyran-3-yl]thieno[3,2-b]pyridin-7-amine

https://huagongshe.com/reaction/711929

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	7-Chloro-6-nitrothieno[3,2-b]pyridine	HCID 14207950	—
Reactant	(3S)-oxan-3-amine hydrochloride	HCID 60145922	—
Solvent	Isopropanol	HCID 3776	—
Product	6-Nitro-N-[(3S)-tetrahydro-2H-pyran-3-yl]thieno[3,2-b]pyridin-7-amine	HCID 86717412	38.4%

Reaction Conditions

Temperature	60 °C

Reaction Steps

A mixture of 7-chloro-6-nitrothieno[3,2-b]pyridine (0.060 g, 0.28 mmol), (3S)-tetrahydro-2H-pyran-3-amine hydrochloride (from J&W Pharmatech, 0.059 g, 0.43 mmol) and N,N-diisopropylethylamine (0.15 mL, 0.84 mmol) in isopropyl alcohol (0.95 mL) was heated at 60° C. overnight. The resulting mixture was concentrated and purified on silica gel (eluting with 0 to 50% ethyl acetate (EtOAc) in hexanes) to give the desired product (30 mg, 38%). LCMS calculated for C12H14N3O3S (M+H)+: m/z=280.1. Found: 280.0.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181271B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-cd9eceaca07a4912b955589051c56fd4
Source note	uspto-grants-2015_11