Water → HCID 178458738, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1.43 g (4.2 mmol) of 3-isopropoxy-5-tert-butoxycarbonyl-6,7-dihydro-4H-thieno[3,2-c]pyridine-2-carboxylic acid in 15 mL of DMF were added 1.07 g (6.6 mmol) of 1,1'-carbonyldiimidazole. The reaction mixture was heated at 85° C. for 2 hours. 5-Aminotetrazole (0.655 g, 7.7 mmol) was added to the reaction mixture in one portion, and the mixture was stirred at 85° C. for 8 hours. The solution was cooled to 24° C. and stirred at that temperature for 18 hours. The reaction mixture was diluted by addition of 100 mL of water and was extracted three times with 50 mL portions of chloroform. The extracts were washed with 50 mL of 2N HCl, water, brine, dried over Na2SO4, and concentrated to dryness by evaporation of the solvent under reduced pressure. The residue was crystallized from 500 mL of diethyl ether to give 1.02 g of 3-isopropoxy-5-tert-butoxycarbonyl-6,7-dihydro-4H-thieno[3,2-c]pyridine-2-carboxylic acid (1H-tetrazol-5-yl) amide, mp 189°-191° C.

Provenance & Evidence