Triacetoxyperiodinane → 2-((2-Chloro-5-cyano-3-(4-oxobutan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

HRID 921855Notes

Reaction equation

HRID 921855 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([CH2:10][CH2:11][OH:12])[CH3:9])=[CH:6][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[C:7]([CH:8]([CH2:10][CH:11]=[O:12])[CH3:9])=[CH:6][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

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 899236462-((2-Chloro-5-cyano-3-(4-hydroxybutan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Product 1

HCID 899237002-((2-Chloro-5-cyano-3-(4-oxobutan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrileYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-((2-chloro-5-cyano-3-(4-hydroxybutan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (179 mg, 0.330 mmol, Example 574D) was taken up in DCM (3 mL) and the solution was cooled to 0° C. Dess-Martin periodinane (168 mg, 0.396 mmol) was added, and the reaction was stirred at 0° C. for 1 h. Some SM still remaining, so an additional 0.4 eq. (56 mg) of Dess-Martin was added, and the reaction was stirred for 30 min. The reaction was quenched with 2M K3PO4 and extracted with DCM. The organic layer was dried over Na2SO4, filtered, and concentrated. The material was purified by flash column chromatography (0%-60% EtOAc/Hex; 40 g column). 2-((2-chloro-5-cyano-3-(4-oxobutan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (131 mg) was obtained as a yellow glass.

Workup

  1. stirringthe reaction was stirred for 30 min
  2. customThe reaction was quenched with 2M K3PO4
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by flash column chromatography (0%-60% EtOAc/Hex; 40 g column)

Sources & evidence

ORD record
ord-54de98e35d85440f9a8f941149f6e67a
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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