Triacetoxyperiodinane → HCID 89923126, compound

HRID 921838Notes

Reaction equation

HRID 921838 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][OH:11])[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[CH:7]=[C:6]([CH2:8][CH2:9][CH:10]=[O:11])[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 89922864HCID 89922864, compound

Product 1

HCID 89923126HCID 89923126, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-((2-chloro-5-cyano-4-(3-hydroxypropyl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (82 mg, 0.155 mmol, Example 566C) was taken up in DCM (1 mL) and cooled to 0° C. Dess-Martin periodinane (85 mg, 0.202 mmol) was added, and the reaction was stirred at room temperature for 1.5 h. An additional 0.2 eq. of Dess-Martin (13 mg) was added and the reaction stirred for 1 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/Hex; 40 g column). 2-((2-chloro-5-cyano-4-(3-oxopropyl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (40 mg) was obtained as a yellow glass.

Workup

  1. stirringthe reaction stirred for 1 h
  2. customThe reaction mixture was quenched with 2M K3PO4 solution
  3. extractionextracted 2× with DCM
  4. dry with materialdried 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-c9664b802a604f87a9eefc849748849e
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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