반응 #487578
ord-fdc6908d19524ed9b2665ac855ac0b3c
반응 방정식
반응물
시약
반응 조건
후처리
- 1기타was consumed (confirmed by HPLC)
- 2workup.STIRRINGthe mixture was stirred 19 hours
- 3농축Concentration in vacuo
- 4기타provided a white solid, which
- 5기타partitioned with water
- 6추출the aqueous layer extracted three times with dichloromethane
- 7세척The combined organic layers were washed with brine
- 8건조dried over anhydrous magnesium sulfate
- 9여과filtered
- 10농축concentrated in vacuo
- 11기타to yield a white solid
실험 절차
1-(1-(5-cyano-2-(3,5-dichlorophenoxy)phenylsulfonyl)-piperidin-4-yl)-3-(2-morpholinoethyl)urea (22) is prepared according to the following method as an alternative to the method of Example 32. 3-(4-aminopiperidin-1-ylsulfonyl)-4-(3,5-dichlorophenoxy)-benzonitrile (1.002 g), prepared according to Example 1, and carbonyldiimidazole (420 mg, 1.1 eq.) were combined in THF (15 mL) and stirred at room temperature. After 5 hours, starting material was consumed (confirmed by HPLC). 4-(2-aminoethyl)morpholine (512 mg, 2.0 eq.) was added and the mixture was stirred 19 hours. Concentration in vacuo provided a white solid, which was resuspended in dichlormethane, partitioned with water, and the aqueous layer extracted three times with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield a white solid. Trituration with isopropyl ether yielded a 96% pure product according to HPLC. The powder was suspended in minimal amounts of hot methanol, stirred at 60° C. for 30 minutes, cooled in an ice bath and vacuum filtered to obtain the product as a white powder (831 mg, 60.7% yield, 98% purity).