Potassium Cyanide → HCID 68580868, compound

HRID 643502Notes

Reaction equation

HRID 643502 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22]3[N:27]=[C:26](Cl)[N:25]=[CH:24][N:23]=3)[CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C-]#N.[K+].[N:33]12CCN(CC1)C[CH2:34]2>O.CS(C)=O.CC(O)=O>[C:1]([O:5][C:6](=[O:29])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22]3[N:27]=[C:26]([C:34]#[N:33])[N:25]=[CH:24][N:23]=3)[CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 9032Potassium CyanideHCID 9237DabcoHCID 86622895HCID 86622895, compound

Product 1

HCID 68580868HCID 68580868, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of [3′-(4-chloro-[1,3,5]triazin-2-ylamino) -biphenyl-4-ylmethyl]-carbamic acid tert-butyl ester (55 mg), potassium cyanide (22 mg) and 1,4-diazabicyclo[2,2,2]octane (4 mg) in water (0.3 ml) and DMSO (1.3 ml) is stirred at 5° C. for 1.5 h. This mixture is acidified with 3 drops of AcOH, quenched with brine and extracted three times with diethyl ether. The combined organic phases are dried over sodium sulfate, the solvent is evaporated and the crude product is purified on silica (4 g) with cyclohexane/EtOAc=4/1 to afford pure [3′-(4-cyano-[1,3,5]triazin-2-ylamino)-biphenyl-4-ylmethyl]-carbamic acid tert-butyl ester.

Workup

  1. customquenched with brine
  2. extractionextracted three times with diethyl ether
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. customthe solvent is evaporated
  5. customthe crude product is purified on silica (4 g) with cyclohexane/EtOAc=4/1

Sources & evidence

ORD record
ord-7caec5cdd8e54f1991139fafe08611be
Source dataset
uspto-grants-2010_04
Patent number
US07700605B2

Reaction notes

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