Pyridine → HCID 136149936, compound

HRID 2263420Notes

Reaction equation

HRID 2263420 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[O:18][C:17]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[N:16][C:15]=2[CH3:31])[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][OH:7])=[NH:5].N1C=CC=CC=1.[C:38]1([O:44]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]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:30])[F:29])=[CH:23][CH:22]=3)=[N:16][C:15]=2[CH3:31])[CH:9]=[CH:8][C:3]=1[C:4]1[NH:5][C:38](=[O:44])[O:7][N:6]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178432700HCID 178432700, compound

Product 1

HCID 136149936HCID 136149936, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

4.4 g crude 2-Chloro-N-hydroxy-4-{4-methyl-2-[2-(4-trifluoromethyl-phenyl)-ethyl]-oxazol-5-ylmethoxy}-benzamidine were dissolved in 20 ml dichloromethane. 0.94 ml pyridine and 1.46 ml phenylchloroformate were added and the mixture stirred at room temperature for ten minutes. The mixture was diluted by the addition of 40 ml acetonitrile and 7.25 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 460 mg 3-(2-chloro-4-{4-methyl-2-[2-(4-trifluoromethyl-phenyl)-ethyl]-oxazol-5-ylmethoxy}-phenyl)-4H-[1,2,4]oxadiazol-5-one.

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-7f55f860cea644d0b0b21954d83a331f
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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