Pyridine → HCID 178432454, compound

HRID 2233314Notes

Reaction equation

HRID 2233314 reaction equation
[Br:1][C:2]1[S:3][C:4]([CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([NH:16][OH:17])=[NH:15])=[C:12]([Cl:20])[CH:11]=2)=[C:5]([CH3:7])[N:6]=1.N1C=CC=CC=1.[C:27]1([O:33]C(Cl)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>ClCCl.C(#N)C>[Br:1][C:2]1[S:3][C:4]([CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]3[NH:16][O:17][C:27](=[O:33])[N:15]=3)=[C:12]([Cl:20])[CH:11]=2)=[C:5]([CH3:7])[N:6]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178432455HCID 178432455, compound

Product 1

HCID 178432454HCID 178432454, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

4-(2-Bromo-4-methyl-thiazol-5-ylmethoxy)-2-chloro-N-hydroxy-benzamidine (199 mg, 0.5 mmol) was dissolved in 6 ml dichloromethane. Pyridine (55 mg, 0.7 mmol) and phenylchloroformate (108 mg, 0.7 mmol) were added and the mixture stirred at room temperature for ten minutes. The mixture was diluted by the addition of 25 ml acetonitrile and 0.4 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 142 mg 3-[4-(2-Bromo-4-methyl-thiazol-5-ylmethoxy)-2-chloro-phenyl]-2H-[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-e7c6b9d6e1814b7789d4d170d7480e39
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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