4-AMIDINOBENZOIC ACID HCL

(6) 4-Amidinobenzoic acid hydrochloride 4-Amidinobenzamide (commercially available one, 7.8 g) is dissolved in water (200 ml), and thereto is added conc. hydrochloric acid (200 ml), and the mixture is stirred at a temperature below 100° C. for 9 hours. The mixture is cooled, and the precipitated crystals are collected by filtration. Yield: 7.6 g MS (SIMS): 165 [M+1]+ 1 H-NMR (CD3 OD) delta (ppm): 7.94 (2H, d, J=8.6 Hz), 8.26 (2H, d, J=8.6 Hz)EXAMPLE 35 1-[[3-[(2-Methylquinolin-8-yl)oxymethyl]-2, 4-dichlorophenyl]sulfonyl]-N-[[1-[4-(aminoiminomethyl)benzoyl]piperidin-4-yl]methyl]-2(S)-pyrrolidinecarboxamide dihydrochloride By following a procedure analogous to Example 23, starting from EXAMPLE 36 1-[[3-[(2-Methylquinolin-8-yl)oxymethyl]-2, 4-dichlorophenyl]sulfonyl]-N-[[1-[2-[4-(aminoiminomethyl)phenyl]-1-oxoethyl]piperidin-4-yl]methyl]-2(S)-pyrrolidinecarboxamide The expected product is obtained in the form of yellow crystals (yield=36percent) by following a procedure analogous to Example 23, starting from (4) This oily substance and 400 mg of sodium hydrogencarbonate were dissolved in a mixture of 25 ml of water and 25 ml of dioxane. To the solution was added, while stirring at room temperature, 250 mg of 4-guanidinobenzoyl chloride hydrochloride. The reaction mixture was adjusted to pH 7 with 1N HCl, to which was added 100 mg of 10percent Pd--C. The mixture was stirred for one hour under hydrogen atmosphere. The catalyst was filtered off. To the filtrate were added 30 ml of dioxane and 400 mg of sodium hydrogencarbonate. To the mixture was added, while stirring vigorously, 230 mg of This oily substance and 400 mg of sodium hydrogencarbonate were dissolved in a mixture of 25 ml of water and 25 ml of dioxane. To the solution was added, while stirring at room temperature, 250 mg of 4-guanidinobenzoyl chloride hydrochloride. The reaction mixture was adjusted to pH 7 with 1N HCl, to which was added 100 mg of 10percent Pd-C. The mixture was stirred for one hour under hydrogen atmosphere. The catalyst was filtered off. To the filtrate were added 30 ml of dioxane and 400 mg of sodium hydrogencarbonate. To the mixture was added, while stirring vigorously, 230 mg of This oily substance and 400 mg of sodium hydrogencarbonate were dissolved in a mixture of 25 ml of water and 25 ml of dioxane. To the solution was added, while stirring at room temperature, 250 mg of 4-guanidinobenzoyl chloride hydrochloride. The reaction mixture was adjusted to pH 7 with 1N HCl, to which was added 100 mg of 10percentPd-C. The mixture was stirred for one hour under hydrogen atmosphere. The catalyst was filtered off. To the filtrate were added 30 ml of dioxane and 400 mg of sodium hydrogencarbonate. To the mixture was added, while stirring vigorously, 230 mg of