Sodium Iodide → HCID 59457494, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[4-(3-chloro-propoxy)-phenyl]-oxazole-4-carbaldehyde i100 (0.042 mmol), 2-methyl-2H-tetrazol-5-ylamine (4.16 mg, 0.042 mmol, 1 eq) and cyanoborohydride supported on polystyrene (26 mg, 0.1 mmol, 2.5 eq) is suspended in tetrahydrofuran (300 μl) containing 10% acetic acid and is stirred at 65° C. overnight. The polystyrene beads are then filtered off and the resulting solution is concentrated to dryness under a stream of nitrogen and taken up in dichloromethane (2 ml). The solution is washed with 1 M potassium hydrogenosulfate (1 ml) and concentrated under reduced pressure. The residue N-({2-[4-(3-chloropropoxy)phenyl]-1,3-oxazol-4-yl}methyl)-2-methyl-2H-tetrazol-5-amine i101 is then treated with a solution of 2-methylpyrrolidine (4 mg, 1 eq) in acetonitrile (300 μl). Sodium carbonate (14 mg, 0.1 mmol, 2 eq) and sodium iodide (15 mg, 0.1 mmol, 2 eq) are added and the suspension is stirred overnight at 80° C. Water (1 ml) is then added and the mixture is extracted with dichloromethane (2×1 ml). The organic phases are concentrated and purified by preparative liquid chromatography (gradient: acetonitrile/water/hydrogen carbonate) to afford 2-methyl-N-[(2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-1,3-oxazol-4-yl)methyl]-2H-tetraazol-5-amine 139.

Provenance & Evidence