1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-amino-5-bromo-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide

To a solution of 6-amino-5-bromo-2-(4-fluorophenyl)-2H-indazole-3-carboxylic acid (1.0 g, 2.8 mmol) in dry DMF (500 mL) were added EDCI (1.1 g, 6.2 mmol) and HOBT (0.5 g, 4.3 mmol). The reaction mixture was stirred at room temperature for 1 h, and then Et3N (5 mL) and MeNH2.HCl (0.9 g, 14.3 mmol) were added to the reaction mixture. After stirring for another 2 hours, the reaction mixture was concentrated in vacuum and 300 mL Na2CO3 (a.q.) was added to the mixture. The resulting solid was filtered to give the crude product, which was purified by column chromatography (PE:EA=3:1) to give 6-amino-5-bromo-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide (0.8 g, yield: 74%). 1H-NMR (CDCl3, 400 MHz) δ 8.10 (s, 1H), 7.55˜7.58 (m, 2H), 7.20˜7.26 (m, 2H), 6.98 (s, 1H), 5.75 (s, 1H), 4.32 (s, 2H), 2.98 (d, J=4.8 Hz, 3H). MS (M+H)+: 363/365.

1. stirringAfter stirring for another 2 hours
2. concentrationthe reaction mixture was concentrated in vacuum and 300 mL Na2CO3 (a.q.)
3. additionwas added to the mixture
4. filtrationThe resulting solid was filtered
5. customto give the crude product, which
6. customwas purified by column chromatography (PE:EA=3:1)

ORDレコード

ord-fe3690130d6448d7b1c0f1070322c0c3

出典データセット

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09243002B2