Pyridine → HCID 135524127, compound

HRID 2233303Notes

Reaction equation

HRID 2233303 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[O:18][C:17]([C:19]3([CH3:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[N:16][C:15]=2[CH3:26])[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][OH:7])=[NH:5].N1C=CC=CC=1.[C:33]1([O:39]C(Cl)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>ClCCl.C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[O:18][C:17]([C:19]3([CH3:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[N:16][C:15]=2[CH3:26])[CH:9]=[CH:8][C:3]=1[C:4]1[NH:5][C:33](=[O:39])[O:7][N:6]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178432498HCID 178432498, compound

Product 1

HCID 135524127HCID 135524127, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

1.39 g 2-Chloro-N-hydroxy-4-[4-methyl-2-(1-methyl-cyclohexyl)-oxazol-5-ylmethoxy]-benzamidine were dissolved in 10 ml dichloromethane. 0.36 ml pyridine and 0.56 ml phenylchloroformate were added and the mixture stirred at room temperature for ten minutes. The mixture was diluted by the addition of 30 ml acetonitrile and 2.75 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 950 mg 3-{2-Chloro-4-[4-methyl-2-(1-methyl-cyclohexyl)-oxazol-5-ylmethoxy]-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-8b948aaab7d34bf6ba644cfdc2b891d6
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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