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ChemicalBook CAS DataBase List AZD2461

AZD2461 synthesis

2synthesis methods
763114-26-7 Synthesis
2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzoic acid

763114-26-7
280 suppliers
$6.00/250mg

4045-25-4 Synthesis
4-Methoxypiperidine hydrochloride

4045-25-4
113 suppliers
$7.00/250mg

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Yield: 72.9%

Reaction Conditions:

with dmap;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane at 20 - 23;Product distribution / selectivity;

Steps:

1
Example 1; 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (231 g, 1206.97 mmol) was added to 4-methoxypiperidine hydrochloride (183 g, 1206.97 mmol), 2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid (300 g, 1005.80 mmol) and 4-dimethylaminopyridine (30.7 g, 251.45 mmol) in DCM (4 L) at 23° C. The resulting suspension was stirred at room temperature over night. The reaction mixture was washed with 2M HCl (5 L) and 50% saturated sodium carbonate (3 L) before being dried over MgSO4, filtered and reduced in-vacuo to give the crude product. This was then slurried in 750 ml of ethyl acetate for 5 days, and then filtered and dried at 45° C. for 5 hours to afford 4-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzyl)phthalazin-1(2H)-one (compound 1)(290 g, 72.9%).1H NMR (400.132 MHz, DMSO) δ 1.26-1.35 (1H, m), 1.40-1.49 (1H, m), 1.69-1.73 (1H, m), 1.84-1.89 (1H, m), 2.99-3.07 (1H, m), 3.25 (3H, s), 3.27-3.34 (2H, m), 3.39-3.44 (1H, m), 3.86-3.95 (1H, m), 4.33 (2H, s), 7.19-7.24 (1H, m), 7.33-7.35 (1H, m), 7.39-7.43 (1H, m), 7.81-7.91 (2H, m), 7.97 (1H, d), 8.27 (1H, d), 12.57 (1H, s); m/z (ES+) (M+H)+=396.31; HPLC tR=1.90 min.FIG. 1 shows the powder XRD pattern of the material produced, which is in Form C.FIG. 2 shows the DSC analysis of the material produced.

References:

ASTRAZENECA AB US2011/15393, 2011, A1 Location in patent:Page/Page column 7

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