Oxalyl chloride → HCID 76601334, compound

Participants

Reaction Steps

Combine 4-biphenylcarboxylic acid (0.124 g, 0.623 mmol), dichloromethane (5.0 mL), and DMF (3 drops) with stirring. Add oxalyl chloride (0.11 mL, 1.25 mmol) and stir the mixture for 2 h at room temperature. Concentrate the mixture in vacuo, add hexane (approximately 10 mL), re-concentrate in vacuo, and re-dissolve in CH2Cl2 (4.0 mL). Transfer the mixture to a 40 mL reaction vial and add a mixture of 2-(3-dimethylamino-pyrrolidin-1-yl)-benzothiazol-6-ylamine (0.109 g, 0.415 mmol) (Example 1, step 3) in CH2Cl2 (2.0 mL). Stir the mixture overnight at room temperature. Dilute the reaction mixture with CH2Cl2 (25 mL), wash with saturated NaHCO3 (aqueous) (25 mL), and extract the aqueous phase with CH2Cl2 (25 mL). Wash the combined organic phases with saturated NaHCO3 (aqueous) (2×25 mL), dry over sodium sulfate, filter, and concentrate in vacuo to yield a yellow solid. Purify the crude product using silica gel chromatography (40 g column, 5% MeOH/CH2Cl2) to afford the title compound (53 mg, 29%). mass spectrum (m/e): 443.4 [M+1], 441.3 [M−1]. 1H NMR (400 MHz, CDCl3): δ 8.69-8.58 (m, 1H), 8.26 (s, 1H), 7.93 (d, 2H, J=8.0 Hz), 7.67 (d, 2H, J=7.6 Hz), 7.59 (d, 2H, J=7.2 Hz), 7.50-7.26 (m, 5H), 3.81 (t, 1H, J=10.4 Hz), 3.72 (t, 1H, J=8.8 Hz), 3.52 (m, 1H), 3.43 (m, 1H), 3.01 (m, 1H), 2.35 (s, 6H), 2.29 (m, 1H), 2.04 (m, 1H).

Provenance & Evidence