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

HRID 2263425
Notes
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Reaction equation

HRID 2263425 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([CH2:11][C:12]3[N:13]=[C:14]([C:33]4[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=4)[S:15][C:16]=3[CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[NH:29][C:28](=[O:30])[O:27][N:26]=4)=[C:21]([O:31][CH3:32])[CH:20]=3)[CH2:7][CH2:6]2)[O:4]CC1.Cl.C(=O)([O-])O.[Na+]>O1CCOCC1>[OH:1][C:5]1([OH:4])[CH2:6][CH2:7][N:8]([CH2:11][C:12]2[N:13]=[C:14]([C:33]3[CH:34]=[CH:35][C:36]([C:39]([F:40])([F:41])[F:42])=[CH:37][CH:38]=3)[S:15][C:16]=2[CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[NH:29][C:28](=[O:30])[O:27][N:26]=3)=[C:21]([O:31][CH3:32])[CH:20]=2)[CH2:9][CH2:10]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 1361500263-{4-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-ylmethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-1,2,4-oxadiazol-5-one

Product 1

HCID 1361500463-{4-[4-(4,4-dihydroxy-piperidin-1-ylmethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-1,2,4-oxadiazol-5-oneYield 62.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 10 mg of 3-{4-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-ylmethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-1,2,4-oxadiazol-5-one in 2 mL of dioxane was added 0.5 mL of a 6N aqueous solution of hydrochloric acid. The resulting mixture was heated to 50° C. for 2 h and then poured into a saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was recrystallized in acetonitrile to give 6 mg of 3-{4-[4-(4,4-dihydroxy-piperidin-1-ylmethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-1,2,4-oxadiazol-5-one as yellowish solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was recrystallized in acetonitrile

Sources & evidence

ORD record
ord-374d833dd3e141ed835c7305320434af
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07851493B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes