Pyridine → HCID 135508486, compound

HRID 2233572Notes

Reaction equation

HRID 2233572 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[S:18][C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[N:16][C:15]=2[CH3:29])[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][OH:7])=[NH:5].N1C=CC=CC=1.[C:36]1([O:42]C(Cl)=O)C=CC=CC=1.C(OCC)(=O)C>ClCCl>[F:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[S:18][C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:28])[F:27])=[CH:21][CH:20]=3)=[N:16][C:15]=2[CH3:29])[CH:9]=[CH:8][C:3]=1[C:4]1[NH:5][C:36](=[O:42])[O:7][N:6]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 15891Phenyl chloroformateHCID 178432506HCID 178432506, compound

Product 1

HCID 135508486HCID 135508486, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

138 mg of 2-Fluoro-N-hydroxy-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-ylmethoxy]-benzamidine were dissolved in 2 ml dichloromethane. 35 μl pyridine and 53 μl phenylchloroformate were added and the mixture stirred at room temperature for thirty minutes. The mixture was diluted by the addition of 20 ml ethyl acetate, washed with brine and dried over MgSO4. The solvent was evaporated in vacuo. The resulting residue was dissolved in 2 ml acetonitrile and 105 μl 1,8-Diazabicyclo[5.4.0]undec-7-ene was 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 70 mg 3-{2-Fluoro-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazole-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 2 ml acetonitrile
  5. addition105 μl 1,8-Diazabicyclo[5.4.0]undec-7-ene was 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-0299eeb0863e4d7eba0b4621a684514f
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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