Cesium carbonate → 8-[(4-Methoxyphenyl)methyl]-12-(3-methyl-6-oxopyridazin-1-yl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one

HRID 707474

Reaction equation

Br[C:2]1[CH:11]=[N:10][C:9]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:7](=[O:21])[N:6]3[N:22]=[CH:23][N:24]=[C:5]3[C:4]=2[CH:3]=1.[CH3:25][C:26]1[CH:27]=[CH:28][C:29](=[O:32])[NH:30][N:31]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]I.O1CCOCC1>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:8]2[C:9]3[N:10]=[CH:11][C:2]([N:30]4[C:29](=[O:32])[CH:28]=[CH:27][C:26]([CH3:25])=[N:31]4)=[CH:3][C:4]=3[C:5]3=[N:24][CH:23]=[N:22][N:6]3[C:7]2=[O:21])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 120 °C

Procedure

9-Bromo-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (75 mg, 0.19 mmol), 6-methylpyridazin-3(2H)-one (43 mg, 0.39 mmol), copper(I) iodide (44 mg, 0.23 mmol), dioxane (3 ml), trans-1,2-diaminocyclohexane (0.030 ml, 0.25 mmol) and cesium carbonate (152 mg, 0.47 mmol) were combined and heated at 120° C. for 12 hours in the microwave. The mixture was filtered and the residue was purified by HPLC to afford 9 mg (11%) of the title compound as a white solid.

Workup

filtrationThe mixture was filtered
customthe residue was purified by HPLC

Sources & evidence

ORD record: ord-d4c999a530154385b21fe8de5c8df8a5
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09175010B2

Linked notes

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