Diethyl Ether → HCID 58976508, compound

HRID 601057Notes

Reaction equation

HRID 601057 reaction equation
CS([C:5]1[N:10]=[C:9]([N:11]2[C:15]([NH2:16])=[N:14][C:13]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:12]2)[CH:8]=[C:7]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:6]=1)(=O)=O.[C-:31]#[N:32].[K+].CCO.C(Cl)Cl.C(OCC)C>CS(C)=O>[NH2:16][C:15]1[N:11]([C:9]2[CH:8]=[C:7]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:6]=[C:5]([C:31]#[N:32])[N:10]=2)[N:12]=[C:13]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:14]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9032Potassium CyanideHCID 21584144Dichloromethane ethanolHCID 58976043HCID 58976043, compound

Product 1

HCID 58976508HCID 58976508, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (50 mg; 0.12 mMol) of 1-(2-methanesulfonyl-6-phenylamino-pyrimidin-4-yl)-N3-phenyl-1H-[1,2,4]triazole-3,5-diamine in 2 mL of DMSO was added 8 mg (0.13 mMol) of potassium cyanide and reaction was stirred for 1 hr at ambient temperature. The solvent was removed under reduced pressure. The residue was triturated with water and the solid was isolated via suction filtration. Column chromatography (SiO2, 5% EtOH—CH2Cl2) followed by trituration with diethyl ether affording 5 mg of an off white powder, (11% yield).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was triturated with water
  3. customthe solid was isolated via suction filtration

Sources & evidence

ORD record
ord-de4500f06e8b4d4a9266b2eb92118b18
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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