Potassium Carbonate → 7-(4-chlorophenyl)-8-(pyridin-4-yl)-2-((5-(trifluoromethyl)pyridin-2-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 2224245Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][N:34]=1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[N:15]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([C:39]([F:41])([F:40])[F:42])=[CH:35][N:34]=4)[N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (32.4 mg, 0.1 mmol), prepared as described in Example 244, K2CO3 (56 mg, 0.4 mmol), and 2-chloromethyl-5-trifluoromethylpyridine hydrochloride (37 mg, 0.4 mmol) in DMF (0.4 mL) was heated at 65° C. for 2 h. Using a similar procedure as described in Example 247, the crude product was obtained. The crude product was purified by reverse phase HPLC to give the title compound, 7-(4-chlorophenyl)-8-(pyridin-4-yl)-2-((5-(trifluoromethyl)pyridin-2-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (27 mg) as a yellow solid. HPLC RT: 2.78 min; M+H=483; 1H NMR (CDCl3): δ 8.82 (s, 1H), 8.62 (m, 2H), 8.24 (s, 1H), 7.91 (m, 1H), 7.38-7.10 (m, 7H), 5.45 (2H).

Workup

customthe crude product was obtained
customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-a063460a4576495ca834a572af08b2dc
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378418B2

Reaction notes

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