反応 #332291

反応方程式

3-chloro-N-hydroxy-4-methanesulfonylamino-5-methyl-benzamidine

HOBt

EDC HCl

2-(1-ethyl-propyl)-6-methoxy-isonicotinic acid

→

title compound

収率 57.8%

N-(2-Chloro-4-{5-[2-(1-ethyl-propyl)-6-methoxy-pyridin-4-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenyl)-methanesulfonamide

収率 57.8%

溶媒

NaHCO3

DMF

反応条件

後処理

1. 1
   workup.ADDITIONis added
2. 2
   抽出extracted twice with EA
3. 3
   乾燥extracts are dried over MgSO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   workup.DISSOLUTIONThe resulting orange oil (65 mg) is dissolved in dioxane (5 mL)
7. 7
   温度heated to 80° C. for 3 h
8. 8
   その他The solvent is removed in vacuo
9. 9
   その他the crude product is purified on prep

実験手順

HOBt (20 mg, 148 μmol) and EDC HCl (28 mg, 148 μmol) are added to a solution of 2-(1-ethyl-propyl)-6-methoxy-isonicotinic acid (30 mg, 134 μmol) in DMF (5 mL). The mixture is stirred at rt for 5 min before 3-chloro-N-hydroxy-4-methanesulfonylamino-5-methyl-benzamidine (38 mg, 136 μmol) is added. The mixture is stirred at rt for 18 h before it is diluted with sat. aq. NaHCO3 solution and extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated. The resulting orange oil (65 mg) is dissolved in dioxane (5 mL) and heated to 80° C. for 3 h. The solvent is removed in vacuo and the crude product is purified on prep. TLC plates using heptane:EA 3:2 to give the title compound (36 mg) as a white solid; LC-MS**: tR=0.88 min, [M+H]+=465.06; 1H NMR (CDCl3): δ0.84 (t, J=7.5 Hz, 6H), 1.69-1.88 (m, 4H), 2.56-2.63 (m, 1H), 2.65 (s, 3H), 3.17 (s, 3H), 4.02 (s, 3H), 6.26 (s, 1H), 7.32 (d, J=1.0 Hz, 1H), 7.43 (d, J=0.8 Hz, 1H), 8.07 (d, J=1.0 Hz, 1H), 8.17 (d, J=1.5 Hz, 1H).

出典