Reaktion #332291

Reaktionsgleichung

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

HOBt

EDC HCl

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

→

title compound

Ausbeute 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

Ausbeute 57.8%

Lösungsmittel

NaHCO3

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added
2. 2
   Extraktionextracted twice with EA
3. 3
   Trocknenextracts are dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   workup.DISSOLUTIONThe resulting orange oil (65 mg) is dissolved in dioxane (5 mL)
7. 7
   Temperaturheated to 80° C. for 3 h
8. 8
   SonstigeThe solvent is removed in vacuo
9. 9
   Sonstigethe crude product is purified on prep

Vorschrift

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).

Quelle