3,6-Dichloropyridazine → 6-(1-(6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)cyclopropyl)quinoline

HRID 1892406Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3([C:14]([NH:16][NH2:17])=O)[CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl:18][C:19]1[N:20]=[N:21][C:22](Cl)=[CH:23][CH:24]=1>C(O)CCC>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]2[N:16]([C:14]([C:11]3([C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:1]=[CH:2][CH:3]=[CH:4]5)[CH2:13][CH2:12]3)=[N:20][N:21]=2)[N:17]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A sealed tube was charged with 1-(quinolin-6-yl)cyclopropanecarbohydrazide (513 mg, 2.26 mmol), 3,6-dichloro-pyridazine (437 mg, 2.93 mmol) and 5 mL of n-butanol. The mixture was heated at 140° C. for 12 h. After cooling, solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel eluting with EtOAc/methanol gradient to afford the title compound (196 mg, 41%). LCMS (method A): [MH]+=322, tR=4.38 min.

Workup

temperatureAfter cooling
customsolvent was removed in vacuo
customthe residue was purified by flash chromatography on silica gel eluting with EtOAc/methanol gradient

Sources & evidence

ORD record: ord-3aa7841f094a42adb8937b44cfe03ba7
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507676B2

Reaction notes

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