Sodium Bicarbonate → HCID 72768218, compound

Participants

Reaction Steps

To a stirred solution of sodium (100 mg, 4.2 mmol) in anhydrous MeOH (4 mL) was added NH2OH.H2O (260 mg, 3.7 mmol) followed by a solution of 4-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-3-methoxymethyl-benzoic acid methyl ester (170 mg, 0.37 mmol) in anhydrous MeOH (4 mL). The mixture was stirred for 16 hours, diluted with CHCl3 (50 mL) and poured into a saturated NaHCO3 solution (50 mL). The aqueous layer was extracted with CHCl3 (5×25 mL). The combined organic portions were dried over Na2SO4 and concentrated. The resultant crude material was purified on a silica gel column (10 g, eluted with 5% NH4OH/10% MeOH/CH2Cl2) and dried under high vacuum to give COMPOUND 46 (60 mg, 35%) as a white solid. 1H NMR (CDCl3) δ 1.57-1.71 (m, 2H), 1.80-2.14 (m, 2H), 2.31-2.40 (m, 2H), 2.44 (s, 6H), 3.25 (s, 3H), 3.61 (s, 2H), 4.12 (s, 4H), 6.61-6.71 (m, 1H), 6.74-6.84 (m, 2H), 6.88-6.97 (m, 1H), 7.20 (s, 3H), 8.22 (s, 2H), 9.85 (s br, 1H); ES-MS m/z 461 (M+H).

Provenance & Evidence