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 658020

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-8472ab8e77174382a88a853d5cb940cf
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076336B2

Linked notes

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