تفاعل #163148

معادلة التفاعل

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

المذيبات

DCM

DCM

ظروف التفاعل

المعالجة

1. 1
   غسيلOrganic phase was washed with dil HCl, saturated solution of NaHCO3, Water, brine
2. 2
   تجفيفdried over Na2SO4
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىto get the crude residue
6. 6
   أخرىThe residue was chromatographed

الإجراء التجريبي

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.

المصدر