Pyridine → 3-{4-[2-(Benzooxazol-2-yl-butyl-amino)-ethyl]-phenyl}-4H-[1,2,4]oxadiazol-5-one

HRID 1441690Notes

Reaction equation

HRID 1441690 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([NH:19][OH:20])=[NH:18])=[CH:15][CH:14]=1.N1C=CC=CC=1.[C:33]1([O:39]C(Cl)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>ClCCl.C(#N)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]2[NH:18][C:33](=[O:39])[O:20][N:19]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178449016HCID 178449016, compound

Product 1

HCID 1361288833-{4-[2-(Benzooxazol-2-yl-butyl-amino)-ethyl]-phenyl}-4H-[1,2,4]oxadiazol-5-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

280 mg 4-[2-(Benzooxazol-2-yl-butyl-amino)-ethyl]-N-hydroxy-benzamidine were dissolved in 5 ml dichloromethane. 78 μl pyridine and 120 μl phenylchloroformate were added and the mixture stirred at room temperature for ten minutes. The mixture was diluted by the addition of 15 ml acetonitrile and 115 μl ml 1,8-Diazabicyclo[5.4.0]undec-7-ene were added. The mixture was stirred at room temperature for 10 minutes. The mixture was evaporated in vacuo and the resulting crude material was purified by reversed phase HPLC to obtain 105 mg 3-{4-[2-(Benzooxazol-2-yl-butyl-amino)-ethyl]-phenyl}-4H-[1,2,4]oxadiazol-5-one as an amorphous lyophilisate.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at room temperature for 10 minutes
  3. customThe mixture was evaporated in vacuo
  4. customthe resulting crude material was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-f99f8cb3233c4709940f4230b9a849d3
Source dataset
uspto-grants-2010_02
Patent number
US07655679B2

Reaction notes

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