1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 44511999, compound

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Reaction Steps

[1-((R)-3-Amino-1-methyl-propyl)-piperidin-4-yl]-(4-ethoxy-phenyl)-(4-methyl-pyridin-3-ylmethyl)-amine (58.0 mg, 0.15 mmol), EDCI (30.9 mg, 0.16 mmol) and HOBT (21.8 mg, 0.16 mmol) were combined in DMF (5 mL) to give a pale yellow solution. To this solution was added 2-chloro-4-methyl-nicotinic acid (27.5 mg, 0.16 mmol) followed by DIPEA (30.6 μL, 0.18 mmol) and the resulting mixture was stirred at room temperature for 16 h. Standard workup according to General Procedure C gave the crude product as a tan oil. Purification by preparative TLC (91:8:1, CH2Cl2/MeOH/NH4OH) afforded 2-chloro-N-((R)-3-{4-[(4-ethoxy-phenyl)-(4-methyl-pyridin-3-ylmethyl)-amino]-piperidin-1-yl}-butyl)-4-methyl-nicotinamide as a white foam (49.2 mg, 61%). 1H NMR (CDCl3) δ 1.02 (d, 3H, J=5 Hz), 1.25 (s, 1H), 1.35 (t, 4H, J=5 Hz), 1.58 (m, 1H), 1.84 (m, 4H), 2.15 (m, 1H), 2.35 (s, 6H), 2.54 (m, 1H), 2.86 (m, 3H), 3.31 (m, 2H), 3.78 (m, 1H), 3.93 (m, 4H), 6.66 (dd, 4H, J=9 Hz, 24 Hz), 7.00 (dd, 2H, J=6 Hz, 18 Hz), 8.01 (d, 1H, J=6 Hz), 8.35 (m, 2H). ES-MS m/z 550 (M+H). Anal. Calcd. For C31H40ClN5O2: C, 67.68; H, 7.33; Cl, 6.44; N, 12.73.

Provenance & Evidence