2-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one → 2-(6-Chloro-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)-1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone

HRID 1524614Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([NH2:11])=[N:9][N:10]=2)[N:7]=1.Br[CH2:13][C:14]([C:16]1[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:19]([OH:26])=[C:18]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:17]=1)=[O:15]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](=[NH:11])[N:9]([CH2:13][C:14]([C:16]3[CH:21]=[C:20]([C:22]([CH3:24])([CH3:23])[CH3:25])[C:19]([OH:26])=[C:18]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:17]=3)=[O:15])[N:10]=2)[N:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamin (W2.001a; 30 mg) was initially charged in DMF (3.5 ml) at RT while stirring, and 2-bromo-1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone (O1.002; 58 mg) predissolved in DMF (0.5 ml) was added dropwise. The reaction mixture was stirred at RT for 30 min and was then heated to 60° C. for 5 h. After standing overnight, the solvent was removed under reduced pressure and the residue was purified by means of preparative HPLC (met. A). The clean product fractions were combined, freed of the acetonitrile under reduced pressure and freeze-dried. 28 mg of the title compound were obtained. LC-MS rt: 1.28 min [M+H]+: 416.1 (met. a)

Workup

additionwas added dropwise
stirringThe reaction mixture was stirred at RT for 30 min
customthe solvent was removed under reduced pressure
customthe residue was purified by means of preparative HPLC (
customfreeze-dried

Sources & evidence

ORD record: ord-1ad902877d2a461d9ccece4b4799f5e7
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079906B2

Reaction notes

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