반응 #2148359

반응 방정식

1-(methoxycarbonyl)cyclopropanecarboxylic acid

HATU

DIPEA

Na2SO4

17

(E)-1-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)-2-hydroxyguanidine

→

methyl 1-(3-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylamino)-1,2,4-oxadiazol-5-yl)cyclopropanecarboxylate

용매

DMF

반응 조건

후처리

1. 1
   기타The consumption of 17
2. 2
   여과Solid was filtered off
3. 3
   workup.DISSOLUTIONthe residue was dissolved in EtOAc (50 mL)
4. 4
   세척The organic layer was washed with water twice
5. 5
   건조dried over Na2SO4
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타to yield a residue which
9. 9
   기타was purified by flash chromatography on silica with 3-5% MeOH in DCM as eluant

실험 절차

To a solution of 1-(methoxycarbonyl)cyclopropanecarboxylic acid (56 mg, 0.39 mmol), HATU (180 mg, 0.47 mmol) and DIPEA (0.082 mL, 0.47 mmol) in dry DMF (2 mL) at rt in the presence of anhydrous Na2SO4 (284 mg, 2.0 mmol) was added 17 (130 mg, 0.39 mmol) slowly. The consumption of 17 was determined to be completed by LC/MS. The mixture was heated at 100° C. for 2 h. Solid was filtered off and the residue was dissolved in EtOAc (50 mL). The organic layer was washed with water twice, dried over Na2SO4, filtered and evaporated to yield a residue which was purified by flash chromatography on silica with 3-5% MeOH in DCM as eluant to yield methyl 1-(3-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylamino)-1,2,4-oxadiazol-5-yl)cyclopropanecarboxylate 23. MS m/z 446.2 (M+1).

출처