반응 #163148

반응 방정식

5-cyclopropyl-1,3,4-thiadiazol-2-amine

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

3-(1-methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoic acid

3-(1-Methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoic acid

Intermediate 1

3-(4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-(1-methyl-2-oxo pyrrolidin-3-yloxy)benzoic acid

→

product

N-(5-Cyclopropyl-1,3,4-thiadiazol-2-yl)-3-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-((1-methyl-2-oxopyrrolidin-3-yl)oxy)benzamide

용매

DCM

DCM

반응 조건

후처리

1. 1
   세척Organic phase was washed with dil HCl, saturated solution of NaHCO3, Water, brine
2. 2
   건조dried over Na2SO4
3. 3
   여과filtered
4. 4
   농축concentrated in vacuo
5. 5
   기타to get the crude residue
6. 6
   기타The residue was chromatographed

실험 절차

4-(Dimethylamino)pyridine (DMAP) (0.149 g), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI.HCl) (0.524 g) were added to a solution of 3-(1-methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoic acid (0.5 g) (Intermediate 1) in dry DCM under nitrogen at 0-5° C. 5-cyclopropyl-1,3,4-thiadiazol-2-amine (0.134 g) was added and the mixture was stirred for 16 h at room temperature. It was diluted with commercially available DCM. Organic phase was washed with dil HCl, saturated solution of NaHCO3, Water, brine, dried over Na2SO4, filtered and concentrated in vacuo to get the crude residue. The residue was chromatographed using silica gel as stationary phase and MeOH: CHCl3 gradient as mobile phase up to yield the product (0.3 g) as a white solid.

출처