2-Dimethylaminopyridine → methyl 3,5-dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)benzoate

A stirred solution of 2,6-dichloro-4-(methoxycarbonyl)benzoic acid (750 mg, 3 mmol, intermediate 32), 1-hydroxy-7-azabenzotriazole (614 mg, 4.5 mmol), dimethylaminopyridine (183 mg, 1.5 mmol), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (1170 mg, 4.5 mmol) in N,N-dimethylacatamide was treated with N-(1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropane carboxamide (605 mg, 3 mmol, intermediate 28) and Hunig's base (1.33 ml, 7.5 mmol). The reaction mixture was stirred at room temperature for about 1 hour and was heated at 50° C. for about 5 hours. To the reaction mixture, ice cold water was added and the precipitated solid was filtered, washed with water and dried. The solid thus obtained was purified by silica gel (100-200 mesh) column chromatography using methanol and dichloromethane gradient elution to afford methyl 3,5-dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)benzoate (600 mg, 47%) as an off-white solid.

1. temperaturewas heated at 50° C. for about 5 hours
2. additionTo the reaction mixture, ice cold water was added
3. filtrationthe precipitated solid was filtered
4. washwashed with water
5. customdried
6. customThe solid thus obtained
7. customwas purified by silica gel (100-200 mesh) column chromatography
8. washmethanol and dichloromethane gradient elution

ORDレコード

ord-ee069834e9ff4838b3cd49ae92d4a49c

出典データセット

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08980911B2