반응 #1614748

반응 방정식

1-{2-[(2S,4R)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidin-1-yl]-2-oxo-ethyl}-6-hydroxy-1H-indole-3-carboxylic acid amide

HCl

Cs2CO3

5-(chloromethyl)-1H-tetrazole

→

title compound

1-{2-[(2S,4R)-2-(3-Chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidin-1-yl]-2-oxo-ethyl}-6-(1H-tetrazol-5-ylmethoxy)-1H-indole-3-carboxylic acid amide

용매

DMSO

Water

반응 조건

후처리

1. 1
   workup.STIRRINGstirring at RT for 36 h
2. 2
   기타to form a precipitate
3. 3
   여과The solid material was filtered off
4. 4
   세척washed with water
5. 5
   기타dried in vacuo

실험 절차

A solution of 1-{2-[(2S,4R)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidin-1-yl]-2-oxo-ethyl}-6-hydroxy-1H-indole-3-carboxylic acid amide Example 578 (148 mg, 0.283 mmol) in DMSO (3 mL) was treated with Cs2CO3 (0.28 g, 0.85 mmol). The mixture was stirred at RT for 5 min, followed by addition of 5-(chloromethyl)-1H-tetrazole (35 mg, 0.098 mmol) and stirring at RT for 36 h. The reaction mixture was neutralised by addition of 1N HCl. Water was then added to the mixture to form a precipitate. The solid material was filtered off, washed with water, and dried in vacuo to afford the title compound as a solid. MS (LC/MS): 573 [M+H]+; tR (HPLC conditions k): 2.92 min.

출처