反応 #1994328

反応方程式

2,6-lutidine

methanesulfonyl chloride

2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazole-3-carboxylic acid

oxalyl chloride

6-amino-2-(4-methoxy-benzyl)-5-methyl-2H-indazole-7-carboxylic acid

→

desired product

7-[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazol-3-yl]-2-(4-methoxy-benzyl)-5-methyl-2H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one

溶媒

acetonitrile

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他After 18 hours of reaction
3. 3
   濃縮the mixture was concentrated under vacuum and water (25 ml)
4. 4
   workup.ADDITIONwas added
5. 5
   抽出The product was extracted with ethyl acetate
6. 6
   その他purified by flash chromatography on silica gel using a gradient from 50% to 100% ethyl acetate in cyclohexane

実験手順

A suspension of 6-amino-2-(4-methoxy-benzyl)-5-methyl-2H-indazole-7-carboxylic acid (0.288 g, 0.925 mmol) in acetonitrile (4 ml) was stirred at 20° C. for 10 minutes before the acyl chloride prepared from 2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazole-3-carboxylic acid and oxalyl chloride (0.265 g, 0.971 mmol) was added. After 45 minutes stirring, 2,6-lutidine (0.215 ml) was added, followed 10 minutes later by methanesulfonyl chloride (0.072 ml, 0.925 mmol). After 18 hours of reaction, the mixture was concentrated under vacuum and water (25 ml) was added. The product was extracted with ethyl acetate and purified by flash chromatography on silica gel using a gradient from 50% to 100% ethyl acetate in cyclohexane. The desired product was obtained as light orange crystals.

出典