Triethylamine → 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)-N-(pyridin-2-ylmethyl)pyrimidine-5-formamide

In THF (50 mL) were dissolved 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acid, pyridine-2-ylmethylamine (69 mg, 0.64 mmol) and triethylamine (0.2 mL). The solution was cooled in an ice bath and HATU (266 mg, 0.70 mmol) was then added. The reaction was conducted at ambient temperature for 18 h. The reaction mixture was concentrated, followed by addition of water and extraction with ethyl acetate. The organic phase was dried, concentrated and purified by silica gel column chromatography (DCM/methanol=50/1) to give 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)-N-(pyridin-2-ylmethyl)pyrimidine-5-formamide (60 mg, 24% yield).

1. temperatureThe solution was cooled in an ice bath
2. concentrationThe reaction mixture was concentrated
3. additionfollowed by addition of water and extraction with ethyl acetate
4. customThe organic phase was dried
5. concentrationconcentrated
6. custompurified by silica gel column chromatography (DCM/methanol=50/1)

ORD-Eintrag

ord-e7b917f0565b461c974aa39589b7b99e

Quelldatensatz

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09359371B2