1-Hydroxybenzotriazole → HCID 18723325, compound

Participants

Reaction Steps

Step 1 (Amide Coupling): 5-Benzimidazole carboxylic acid (0.50 g, 3.1 mmol), EDC.HCl (0.72 g, 3.7 mmol) and HOBt (0.58 mg, 3.7 mmol) in dichloromethane (11 mL) was stirred at room temperature for 10 minutes. 4-Amino-piperidine-1-carboxylic acid tert-butyl ester (0.70 g, 3.4 mmol) and DIPEA (0.59 ml, 3.4 mmol) were added and the mixture was stirred for 3 hours. The mixture was then partitioned between EtOAc and sat. aqueous Na2CO3. The layers were separated and the aqueous layer was extracted with EtOAc (×3). The combined organic layers were washed with water, brine and dried (MgSO4). The solvent was evaporated in vacuo to give 3H-benzoimidazole-5-carboxylic acid (1-methyl-piperidin-4-yl)-amide.

Provenance & Evidence