4-Pyridineethanol → 3-Amino-5-chloro-4-methyl-6-(2-pyridin-4-yl-ethoxy)-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

Temperatur

75 °C

To a solution of 4-pyridineethanol (0.862 g, 7.0 mmol) in THF (3 ml) at room temperature is added dropwise a solution of lithium bis(trimethylsilyl)amide (1.0 M in hexanes)(3.50 ml, 3.50 mmol). The reaction mixture is stirred for 15 minutes and then is treated with 3-amino-5-chloro-6-methanesulfinyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide (0.345 g, 1.00 mmol). The reaction mixture is heated at 75° C. in a sealed tube for 1.5 hours, cooled to room temperature, and then quenched by the addition of water (10 ml). The reaction mixture is transferred to an erlenmeyer flask and diluted to 75 ml with water. The mixture is cooled to 0° C. and stirred. During this time, a yellow precipitate is formed. This solid is collected by filtration and slurried in a 2:1 EtOAc:hexane mixture. This slurry is stirred for 10 minutes, filtered, and the collected solid is placed in the vacuum oven to dry (60° C. for 16 hours). This affords the title compound as a yellow solid (0.231 g, 57%). Mass (m/z): 403.1 (M++1), 401.1 (M+−1).

1. temperaturecooled to room temperature
2. customquenched by the addition of water (10 ml)
3. customThe reaction mixture is transferred to an erlenmeyer flask
4. additiondiluted to 75 ml with water
5. temperatureThe mixture is cooled to 0° C.
6. stirringstirred
7. customDuring this time, a yellow precipitate is formed
8. filtrationThis solid is collected by filtration
9. stirringThis slurry is stirred for 10 minutes
10. filtrationfiltered
11. customto dry (60° C. for 16 hours)

ORD-Eintrag

ord-366370a7edb44f2a91d285fb309ffe11

Quelldatensatz

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08071776B2