Benzylamine → N-benzyl-2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)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 (16 g, 42.8 mmol), benzylamine (5.0 g, 47 mmol), HATU (17.9 g, 47 mmol) and DIEA (11 g, 85.6 mmol). The reaction mixture was stirred at ambient temperature overnight and concentrated, followed by addition of DCM (500 mL). After the completion of the reaction, water (500 mL×4) was added to the reaction mixture for extraction. The organic phase was concentrated. The crude product was purified by silica gel column chromatography to give N-benzyl-2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)pyrimidine-5-formamide as the product (50 mg, 24% yield).

1. concentrationconcentrated
2. additionfollowed by addition of DCM (500 mL)
3. customAfter the completion of the reaction, water (500 mL×4)
4. additionwas added to the reaction mixture for extraction
5. concentrationThe organic phase was concentrated
6. customThe crude product was purified by silica gel column chromatography

ORDレコード

ord-fd39ec7d80324ff0845654f678eb7da1

出典データセット

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09359371B2