2-amino-N-(4-chlorophenyl)acetamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzaldehyde, hydrobromide salt (0.25 g, 0.52 mmol), 2-amino-N-(4-chloro-phenyl)-acetamide (114 mg, 0.62 mmol) and sodium triacetoxyborohydride (0.183 g, 0.87 mmol) in 1,2-dichloroethane (25 ml) was stirred at 0° C. and then slowly warmed to rt where it was maintained for 16 h. After this time a saturated solution of KHSO4 was introduced and the suspension was filtered. The collected solid was washed with MeOH and H2O and then dried to provide N-(3-chloro-phenyl)-2-(4-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzylamino)-acetamide (50 mg, 17%). HPLC-MS 572 [M+1]+, 287. was maintained for 16 h the suspension was filtered The collected solid was washed with MeOH and H2O dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzaldehyde, hydrobromide salt (0.25 g, 0.52 mmol), 2-amino-N-(4-chloro-phenyl)-acetamide (114 mg, 0.62 mmol) and sodium triacetoxyborohydride (0.183 g, 0.87 mmol) in 1,2-dichloroethane (25 ml) was stirred at 0° C. and then slowly warmed to rt where it was maintained for 16 h. After this time a saturated solution of KHSO4 was introduced and the suspension was filtered. The collected solid was washed with MeOH and H2O and then dried to provide N-(3-chloro-phenyl)-2-(4-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzylamino)-acetamide (50 mg, 17%). HPLC-MS 572 [M+1]+, 287. was maintained for 16 h the suspension was filtered The collected solid was washed with MeOH and H2O dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzaldehyde, hydrobromide salt (0.25 g, 0.52 mmol), 2-amino-N-(4-chloro-phenyl)-acetamide (114 mg, 0.62 mmol) and sodium triacetoxyborohydride (0.183 g, 0.87 mmol) in 1,2-dichloroethane (25 ml) was stirred at 0° C. and then slowly warmed to rt where it was maintained for 16 h. After this time a saturated solution of KHSO4 was introduced and the suspension was filtered. The collected solid was washed with MeOH and H2O and then dried to provide N-(3-chloro-phenyl)-2-(4-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzylamino)-acetamide (50 mg, 17%). HPLC-MS 572 [M+1]+, 287. was maintained for 16 h the suspension was filtered The collected solid was washed with MeOH and H2O dried