Pyridine → HCID 11690740, compound

Participants

Reaction Steps

Add oxalyl chloride (0.20 mL, 2.30 mmol) and 3 drops of DMF to a stirring suspension of Biphenyl-4-carboxylic acid (0.240 g, 1.15 mmol) in CH2Cl2 (5.0 mL). Stir the reaction mixture at room temperature for 2 h. Concentrate the mixture in vacuo, add n-hexane, re-concentrate, and re-dissolve in CH2Cl2. Add the resultant biphenyl-4-carbonyl chloride solution to a mixture of rac-N2-methyl-N2-(1-methyl-piperidin-4-yl)-benzooxazole-2,5-diamine (0.200 g, 0.768 mmol) and pyridine (0.06 mL) in CH2Cl2 (10 mL). Shake the reaction mixture overnight at room temperature. Wash the mixture with saturated NaHCO3 (aqueous) (2×25 mL), dry the organic phase over Na2SO4, filter, and concentrate the mixture in vacuo. Subject the residue to silica gel 130 flash column chromatography (5×4 g columns, eluting with 5% 2N NH3 in MeOH/CH2Cl2) to yield the desired product (0.168 g, 50%). mass spectrum (m/e): 441.3 (M+1). 1H NMR (400 MHz, CD3OD): δ 8.01-7.97 (m, 2H), 7.74-7.70 (m, 3H), 7.67-7.64 (m, 2H), 7.48-7.42 (m, 2H), 7.39-7.31 (m, 2H), 7.26 (d, J=8.4 Hz, 1H), 4.12-4.02 (m, 1H), 3.06 (s, 3H), 2.97 (d, J=12.0 Hz, 2H), 2.30 (s, 3H), 2.17 (dt, J=12.4, 2.8 Hz, 2H), 1.91 (dq, J=12.0, 4.0 Hz, 2H), 1.76 (d, J=12.6 Hz, 2H).

Provenance & Evidence