Réaction #1509576

Équation de réaction

1-[1-(4-Chloro-3-methyl-benzyl)-piperidin-4-yl]-5-oxo-pyrrolidine-2-carboxylic acid

DIPEA

DIPEA

HATU

3-Bromo-5-(1-methyl-1H-tetrazol-5-yl)-phenylamine

→

title compound

1-[1-(4-Chloro-3-methyl-benzyl)-piperidin-4-yl]-5-oxo-pyrrolidine-2-carboxylic acid [3-bromo-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-amide

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   FiltrationThe reaction mixture was filtered
2. 2
   Autrethe filtrate partitioned between water and EtOAc
3. 3
   AutreThe organic layer was separated
4. 4
   Autredried
5. 5
   Concentrationconcentrated in vacuum
6. 6
   Autrethe residue purified by flash chromatography (DCM:MeOH 100:0 to 95:5 gradient)

Mode opératoire

To a solution of 1-[1-(4-Chloro-3-methyl-benzyl)-piperidin-4-yl]-5-oxo-pyrrolidine-2-carboxylic acid as DIPEA salt (2.6 g) in DMF (100 ml) was added DIPEA (2.1 g), and HATU (4 g). 3-Bromo-5-(1-methyl-1H-tetrazol-5-yl)-phenylamine (1.4 g) was added and the reaction stirred overnight at rt. The reaction mixture was filtered and the filtrate partitioned between water and EtOAc. The organic layer was separated, dried and concentrated in vacuum and the residue purified by flash chromatography (DCM:MeOH 100:0 to 95:5 gradient) to give the title compound (400 mg). Rf=0.19 (95:5 DCM:MeOH).

Source