Acetic Acid → HCID 68579161, compound

HRID 643500Notes

Reaction equation

HRID 643500 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]([O:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24](Cl)[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.CC(O)=O>O.CS(C)=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]([O:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]([C:34]#[N:33])[N:23]=3)[CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 9237DabcoHCID 86622894HCID 86622894, compound

Product 1

HCID 68579161HCID 68579161, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of [3′-(2-chloro-pyrimidin-4-yloxy)-biphenyl-4-ylmethyl]-carbamic acid tert-butyl ester (161 mg), potassium cyanide (76 mg) and 1,4-diazabicyclo[2,2,2]octane (13 mg) in water (0.4 ml) and DMSO (2 ml) is left at 5° C. for 4 h. This mixture is acidified with AcOH to pH 4-5, quenched with brine and extracted twice with diethyl ether. The combined organic phases are dried over sodium sulfate, the solvent is evaporated and the crude product is purified on silica (15 g) with cyclohexane/EtOAc=5/1 to afford pure [3′-(2-cyano-pyrimidin-4-yloxy)-biphenyl-4-ylmethyl]-carbamic acid tert-butyl ester.

Workup

  1. customquenched with brine
  2. extractionextracted twice 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 (15 g) with cyclohexane/EtOAc=5/1

Sources & evidence

ORD record
ord-e94a73e1394a40889c7b56d585feaeb0
Source dataset
uspto-grants-2010_04
Patent number
US07700605B2

Reaction notes

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