Hydrochloric Acid → 3-{2-methoxy-4-[4-(1-oxo-1lambda4-thiomorpholin-4-ylmethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-1,2,4-oxadiazol-5-one

HRID 2263426Notes

Reaction equation

HRID 2263426 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[N:13][C:12]=2[CH2:26][N:27]2[CH2:32][CH2:31][S:30][CH2:29][CH2:28]2)[CH:6]=[CH:5][C:4]=1[C:33]1[NH:37][C:36](=[O:38])[O:35][N:34]=1.Cl.C[OH:41]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:25])[F:24])=[CH:18][CH:17]=3)=[N:13][C:12]=2[CH2:26][N:27]2[CH2:32][CH2:31][S:30](=[O:41])[CH2:29][CH2:28]2)[CH:6]=[CH:5][C:4]=1[C:33]1[NH:37][C:36](=[O:38])[O:35][N:34]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1361499783-{2-methoxy-4-[4-thiomorpholin-4-ylmethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one

Product 1

HCID 1361500393-{2-methoxy-4-[4-(1-oxo-1lambda4-thiomorpholin-4-ylmethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-1,2,4-oxadiazol-5-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 80 mg of 3-{2-methoxy-4-[4-thiomorpholin-4-ylmethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one in 1 mL of methanol was added 2 mL of a 2N solution of hydrochloric acid in diethylether. The resulting mixture was concentrated under reduced pressure. To a solution of the residue in 1 mL of acetonitrile were added 1 mL of water and 88 mg of Oxone®. The resulting mixture was stirred at room temperature for 1 h, then poured into water and extracted with dichloromethane. The organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient of methanol in dichloromethane) to give 10.5 mg of 3-{2-methoxy-4-[4-(1-oxo-1λ4-thiomorpholin-4-ylmethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-1,2,4-oxadiazol-5-one as white solid.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. additionTo a solution of the residue in 1 mL of acetonitrile were added 1 mL of water and 88 mg of Oxone®
  3. additionpoured into water
  4. extractionextracted with dichloromethane
  5. washThe organic extracts were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by column chromatography on silica gel (gradient of methanol in dichloromethane)

Sources & evidence

ORD record
ord-50b433cb6cae4ea2807e0b35fb94a4c0
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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