Reaction #1509576

Reaction equation

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

Solvents

DMF

Conditions

Workup

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

Procedure

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