Sodium Bicarbonate → 6-((6-Phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoxaline

HRID 1511327Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12](OC(C)(C)C)=O)=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.[C:19]1([C:25]2[N:30]=[N:29][C:28]([NH:31][NH2:32])=[CH:27][CH:26]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>O1CCOCC1.CCOC(C)=O>[C:19]1([C:25]2[CH:26]=[CH:27][C:28]3[N:29]([C:12]([CH2:11][C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:1]=[CH:2][CH:3]=[N:4]5)=[N:32][N:31]=3)[N:30]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of tert-butyl 2-(quinoxalin-6-yl)acetate (0.15 g, 0.6 mmol), 1-(6-phenylpyridazin-3-yl)hydrazine (0.1 g, 0.7 mmol) and p-toluenesulfonic acid monohydrate (0.1 g, 0.6 mmol) in 3 mL of dioxane was heated with microwave at 150° C. for 1 hour in a microwave tube. The mixture was diluted with 70 mL of EtOAc and 40 mL of satd. NaHCO3 solution. The organic phase was separated and was washed with 40 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc to 15% MeOH/EtOAc) to give light yellow solid as desired product 6-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoxaline.

Workup

customThe organic phase was separated
washwas washed with 40 mL of brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (EtOAc to 15% MeOH/EtOAc)

Sources & evidence

ORD record: ord-667e46b195db4058916adf29de778b4e
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08212041B2

Reaction notes

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