ChemicalBook CAS DataBase List AZD3514

AZD3514 synthesis

15synthesis methods

Product Name:AZD3514
CAS Number:1240299-33-5
Molecular formula:C25H32F3N7O2
Molecular Weight:519.56

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

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Yield: 88%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in methanol at 50; under 3750.38 Torr; for 10 h;Product distribution / selectivity;Autoclave;

Steps:

5.5
Example 5.5; Alternative route for the preparation of 6-(4-{4-[2-(4-acetylpiperazin-l- vDethoxyl phenyllpiperidin- l-vD-3-f trifluoromethyl)-7.,8-(iihv(iro [ 1 ,2,41 triazolo [4,3- blpyridazine Form A; Methanol (375.0 mL) was added to 6-[4-[4-[2-(4-acetylpiperazin-l- yl)ethoxy]phenyl]piperidin-l-yl]-3-(trifluoromethyl)[ 1,2,4] triazolo[4,3-b]pyridazine (25.0 g, 48 m mol) in a 2.0 L autoclave reactor and to this was added 10% Pd/C (12.5 g, 50% w/w) paste at 22-25°C under nitrogen gas atmosphere. The reaction was performed under hydrogen pressure (5.0 bar) at 50⁰C temperature for 10.0 h. The reaction mass was cooled to room temperature and the catalyst removed by filtration. Filtered cake was washed with methanol. The solvent was evaporated and the residue was azeotropically distilled by ethylacetate (2 x 125.0 mL) at 40⁰C under reduced pressure to 3.0 rel vol (75.0 mL). Drop wise addition of tert-butylmethylether (MTBE, 375.0 mL) to the reaction mass resulted in solid material, which was collected by filtration and washed with MTBE (50.0 mL). The material was dried under reduced pressure with nitrogen gas bleed at 50⁰C to afford the desired product 6-(4-{4-[2-(4-acetylpiperazin-l-yl)ethoxy]phenyl}piperidin-l-yl)-3- (trifluoromethyl)-7,8-dihydro[l,2,4]triazolo [4,3-b]pyridazine (22.3 g, 88%) as a white color free flowing solid. The isolated material was confirmed by XRPD as Form A. IH NMR (400.13 MHz, CDC13): δ 1.62 (2H, m), 1.88 (2H, m), 2.02 (3H, s), 2.49 (4H, m), 2.65 - 2.78 (5H, m), 2.94 (2H, m), 3.15 (2H, t), 3.42 (2H, m), 3.57 (2H, m), 4.03 (2H, t), 4.24 (2H, m), 6.80 (2H, d), 7.06 (2H, d); m/z = 520 [M+H]+.

References:

ASTRAZENECA AB;ASTRAZENECA UK LIMITED;BRADBURY, Robert, Hugh;CARR, Gregory, Richard;RABOW, Alfred, Arthur;RAO KORUPOJU, Srinivasa;TUMMA, Harikrishna WO2010/92371, 2010, A1 Location in patent:Page/Page column 81-82

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1240299-33-5
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75-36-5 Synthesis

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19099-93-5 Synthesis

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$5.00/1g

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benzyl 4-(4-hydroxyphenyl)-3,6-dihydropyridine-1(2H)-carboxylate

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References