反応 #163151

反応方程式

2-amino-4-methyl thiazole

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

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

→

titled compound

3-(4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-(1-methyl-2-oxopyrrolidin-3-yloxy)-N-(4-methylthiazol-2-yl)benzamide

溶媒

DCM

DCM

反応条件

後処理

1. 1
   洗浄Organic phase was washed with dil HCl, saturated solution of NaHCO3, water, brine
2. 2
   乾燥dried over Na2SO4
3. 3
   ろ過filtered
4. 4
   濃縮concentrated in vacuo
5. 5
   その他to get the crude residue
6. 6
   その他The residue was chromatographed

実験手順

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. 2-amino-4-methyl thiazole (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 to yield pure titled compound (0.3 g) as a white solid.

出典