ChemicalBook CAS DataBase List AMG 925

AMG 925 synthesis

14synthesis methods

Product Name:AMG 925
CAS Number:1401033-86-0
Molecular formula:C26H29N7O2
Molecular Weight:471.55

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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1401033-86-0
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$25.00/1mg

Yield: 99%

Reaction Conditions:

with sodium methylate in methanol;dichloromethane at 20; for 1 h;

Steps:

5
To a solution of 2-(2-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)-2-oxoethyl acetate (514 mg, 1.0 mmol) in DCM (7.5 mL) and MeOH (2.5 mL) was added 0.5 M sodium methoxide solution in MeOH (0.30 mL, 0.15 mmol), and the reaction mixture was stirred at room temperature for 1 hour and monitored using LCMS. Upon completion, the reaction mixture was concentrated. The residue was treated with EtOH (5 mL) and water (10 mL) to provide a solid which was collected by filtration, washed with water, and dried in a vacuum oven at 55° C. overnight to give the title compound (5) as a white solid (468 mg, 99% yield). ¹H NMR (500 MHz, acetic acid-d₄, 373 K) δ ppm 1.09 (3H, d, J=6.5 Hz), 1.31-1.43 (2H, m), 1.70-1.80 (1H, m), 1.99-2.03 (2H, m), 2.06-2.13 (2H, m), 2.68 (2H, dq, J=3.3, 12.7 Hz), 3.10 (2H, t, J=5.4 Hz), 3.88 (2H, br. s.), 4.46 (2H, br. s.), 4.77 (2H, br. s), 4.90 (1H, tt, J=3.9, 12.4 Hz), 7.76 (1H, d, J=8.5 Hz), 8.33 (1H, d, J=8.5 Hz), 8.40 (1H, d, J=6.0 Hz), 8.63 (1H, d, J=6.0 Hz), 9.35 (1H, s), 9.43 (1H, s) ppm; LCMS m/z: 472 (M+1).

References:

Amgen Inc. US2012/244110, 2012, A1 Location in patent:Page/Page column 66

79-14-1 Synthesis