반응 #1779399

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Sodium triacetoxyborohydride

methanol

formaldehyde

4-[2-(1-Azetidin-3-yl-1H-pyrazol-5-yl)-4-fluorophenoxy]-5-chloro-2-flouro-N-1,3-thiazol-4-ylbenzenesulfonamide

→

title compound

5-Chloro-2-fluoro-4-{4-fluoro-2-[1-(1-methylazetidin-3-yl)-1H-pyrazol-5-yl]phenoxy}-N-1,3-thiazol-4-ylbenzenesulfonamide

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGthe solution stirred for 3 hours
2. 2
   기타The solvents were removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate
4. 4
   추출extracted with saturated aqueous sodium hydrogencarbonate solution (2×10 ml) and brine (2×10 ml)
5. 5
   기타The organic layer was separated
6. 6
   건조dried over sodium sulphate
7. 7
   여과filtered
8. 8
   기타evaporated
9. 9
   기타to give a solid
10. 10
    기타The compound was purified

실험 절차

4-[2-(1-Azetidin-3-yl-1H-pyrazol-5-yl)-4-fluorophenoxy]-5-chloro-2-flouro-N-1,3-thiazol-4-ylbenzenesulfonamide (Example 808, 29 mg, 0.052 mmol) was stirred in dichloromethane (2 ml), methanol (0.2 ml), aqueous formaldehyde (0.015 ml of 37% wt/vol) added and the reaction stirred at room temperature for a further 30 minutes. Sodium triacetoxyborohydride (37 mg, 0.172 mmol) was added and the solution stirred for 3 hours. The solvents were removed in vacuo and the residue dissolved in ethyl acetate and extracted with saturated aqueous sodium hydrogencarbonate solution (2×10 ml) and brine (2×10 ml). The organic layer was separated, dried over sodium sulphate, filtered and evaporated to give a solid. The compound was purified using preparative HPLC to afford the title compound. Yield 15.9 mg 57%.

출처