Triacetoxyperiodinane → HCID 89922524, compound

HRID 921848Notes

Reaction equation

HRID 921848 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([CH3:11])[CH2:9][OH:10])=[CH:6][C:5]([C:12]#[N:13])=[CH:4][C:3]=1[NH:14][C:15]1[N:20]=[C:19]([N:21]([CH:31]2[CH2:33][CH2:32]2)[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:18]2=[N:34][CH:35]=[C:36]([C:37]#[N:38])[N:17]2[N:16]=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]([CH3:11])[CH:9]=[O:10])=[CH:6][C:5]([C:12]#[N:13])=[CH:4][C:3]=1[NH:14][C:15]1[N:20]=[C:19]([N:21]([CH:31]2[CH2:32][CH2:33]2)[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:18]2=[N:34][CH:35]=[C:36]([C:37]#[N:38])[N:17]2[N:16]=1

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 89922862HCID 89922862, compound

Product 1

HCID 89922524HCID 89922524, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-((2-chloro-5-cyano-3-(1-hydroxypropan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (37 mg, 0.070 mmol) was taken up in DCM (1 mL) and the solution was cooled to 0° C. Dess-Martin periodinane (35.6 mg, 0.084 mmol) was added, and the reaction was stirred at 0° C. for 1.5 h. Some SM still remaining, so an additional 0.4 eq. (12 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; 12 g column). 2-((2-chloro-5-cyano-3-(1-oxopropan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (25 mg) was obtained as a glassy liquid.

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; 12 g column)

Sources & evidence

ORD record
ord-ad29713f89d8402ca0dacc569958619d
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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