Acetic Acid → HCID 22293389, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the compound of Example 200, Step C (0.210 g, 0.60 mmol) in dichloroethane (5 mL) in a resealable tube was added acetic acid (0.188 mL, 3.28 mmol), methyl amine (2.0 M in MeOH, 1.64 mL, 3.28 mmol) and NaB(OAc)3H (0.951 g, 4.48 mmol), the tube was sealed and the reaction mixture was heated to 70° C. for 30 h. The reaction mixture was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate solution. The organic layer was removed and the aqueous layer was washed twice with CH2Cl2, the combined organic layers were washed with a saturated aqueous brine solution, dried over Na2SO4, filtered and concentrated under vacuum. Purification by silica gel chromatography employing 5-20% EtOAc/CH2Cl2 as the eluant afforded the less polar isomer of Example 200, Step D (0.034 g) as well as the more polar isomer (0.046 g). Example 200, Step D less polar isomer: +APcI MS (M+1)+ 335; 1H NMR (400 MHz, CDCl3) δ: 7.03-7.37 (arom, series of m, 10 H), 3.54 (m, 2H), 3.24 (m, 1H), 2.70 (s, 3H). More polar isomer: +APcI MS (M+1)+ 335; 1H NMR (400 MHz, CDCl3) δ: 7.15-7.33 (arom, series of m, 10 H), 3.59 (d, 1H), 3,43 (d, 1H), 2.74 (s, 3H).

Provenance & Evidence