Triacetoxyperiodinane → HCID 89922850, compound

HRID 921842Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[C:5]([C:13]#[N:14])=[CH:4][C:3]=1[NH:15][C:16]1[N:21]=[C:20]([N:22]([CH:32]2[CH2:34][CH2:33]2)[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:19]2=[N:35][CH:36]=[C:37]([C:38]#[N:39])[N:18]2[N:17]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH:11]=[O:12])[C:5]([C:13]#[N:14])=[CH:4][C:3]=1[NH:15][C:16]1[N:21]=[C:20]([N:22]([CH:32]2[CH2:33][CH2:34]2)[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:19]2=[N:35][CH:36]=[C:37]([C:38]#[N:39])[N:18]2[N:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-((2-chloro-5-cyano-4-(4-hydroxybutyl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (186 mg, 0.343 mmol) was taken up in DCM (3 mL) and cooled to 0° C. Dess-Martin periodinane (189 mg, 0.445 mmol) was added, and the reaction was stirred at room temperature for 1.5 h. The reaction mixture was quenched with 2M K3PO4 solution and extracted 2× with DCM. The organic layers were combined, dried over Na2SO4, filtered, and concentrated. The material was purified by flash column chromatography (0-60% EtOAc/IIex; 40 g column). 2-((2-chloro-5-cyano-4-(4-oxobutyl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (135 mg) was obtained as a yellow glass.

Workup

customThe reaction mixture was quenched with 2M K3PO4 solution
extractionextracted 2× with DCM
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe material was purified by flash column chromatography (0-60% EtOAc/IIex; 40 g column)

Sources & evidence

ORD record: ord-2803797fb36543298f9c8eef0555bfb6
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273057B2

Reaction notes

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