Imidazole → 6-(1-{6-[3-(1H-imidazol-1-yl)phenyl][1,2,4]triazolo[4,3-b][1,2,4]triazin-3-yl}cyclopropyl)quinoline

HRID 1099043Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([C:14]([C:17]4([C:20]5[CH:21]=[C:22]6[C:27](=[CH:28][CH:29]=5)[N:26]=[CH:25][CH:24]=[CH:23]6)[CH2:19][CH2:18]4)=[N:15][N:16]=3)[N:13]=2)[CH:5]=[CH:6][CH:7]=1.[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1.[I-].[Na+].CN[C@H]1CCCC[C@@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu]I>[N:30]1([C:2]2[CH:3]=[C:4]([C:8]3[CH:9]=[N:10][C:11]4[N:12]([C:14]([C:17]5([C:20]6[CH:21]=[C:22]7[C:27](=[CH:28][CH:29]=6)[N:26]=[CH:25][CH:24]=[CH:23]7)[CH2:19][CH2:18]5)=[N:15][N:16]=4)[N:13]=3)[CH:5]=[CH:6][CH:7]=2)[CH:34]=[CH:33][N:32]=[CH:31]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 6-{1-[6-(3-bromophenyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-yl]cyclopropyl}quinoline (20 mg, 0.04 mmol) in 1,4-dioxane (1 mL) was added 1H-imidazole (4.61 mg, 0.0677 mmol), sodium iodide (14 mg, 0.090 mmol), (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (1 mg, 0.009 mmol), copper(I) iodide (0.8 mg, 0.004 mmol), and cesium carbonate (31 mg, 0.095 mmol), then the mixture was heated at 120° C. overnight. The reaction mixture was cooled to RT and filtered. The filtrate was diluted with MeOH and purified by RP-HPLC (pH=10) to afford the desired compound 8 mg (40%) LCMS: (M+H)+=431.1.

Workup

temperatureThe reaction mixture was cooled to RT
filtrationfiltered
additionThe filtrate was diluted with MeOH
custompurified by RP-HPLC (pH=10)

Sources & evidence

ORD record: ord-e8b17beec8964289a18ff02a3c3a8738
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143251B2

Reaction notes

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