Pyridine → HCID 135870789, compound

HRID 2233579Notes

Reaction equation

HRID 2233579 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH:21][OH:22])=[NH:20])=[C:14]([Cl:23])[CH:13]=1)[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.[C:40]1([O:46]C(Cl)=O)C=CC=CC=1.C(OCC)(=O)C>ClCCl>[CH2:1]([C:5]1[N:6]=[C:7]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:29]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]2[NH:20][C:40](=[O:46])[O:22][N:21]=2)=[C:14]([Cl:23])[CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 15891Phenyl chloroformateHCID 178441582HCID 178441582, compound

Product 1

HCID 135870789HCID 135870789, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.3 g crude 2-{4-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-chloro-phenyl}-N-hydroxy-acetamidine were dissolved in 30 ml dichloromethane. 0.46 ml pyridine and 0.71 ml phenylchloroformate were added and the mixture stirred at room temperature for ten minutes. The mixture was diluted by the addition of 150 ml ethyl acetate, washed with brine and dried over MgSO4. The solvent was evaporated in vacuo. The resulting residue was dissolved in 20 ml acetonitrile and 0.70 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 820 mg 3-{4-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-chloro-benzyl}-4H-[1,2,4]oxadiazol-5-one as an amorphous lyophilisate.

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated in vacuo
  4. dissolutionThe resulting residue was dissolved in 20 ml acetonitrile
  5. addition0.70 ml 1,8-Diazabicyclo[5.4.0]undec-7-ene were added
  6. stirringThe mixture was stirred at room temperature for 10 minutes
  7. customThe mixture was evaporated in vacuo
  8. customthe resulting crude material was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-d195e021c45c48caa4556a9439e4cce1
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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