Hydrochloric Acid → HCID 178435094, compound

HRID 2221709Notes

Reaction equation

HRID 2221709 reaction equation
COC[O:4][C:5]1[C:9](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[S:15][C:16]=2[CH3:17])=[CH:8][N:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:6]=1.Cl>CO>[OH:4][C:5]1[C:9](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[S:15][C:16]=2[CH3:17])=[CH:8][N:7]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23076341HCID 23076341, compound

Product 1

HCID 178435094HCID 178435094, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl 4-(4-{(E)-2-[3-(methoxymethoxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-5-methyl-1,3-thiazol-2-yl)piperazine-1-carboxylate (1.1 g) in methanol (20 mL) was added concentrated hydrochloric acid (0.3 mL) at room temperature, and the mixture was stirred at 50° C. for 2 hrs. The reaction mixture was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate (15 mL), di-tert-butyl dicarbonate (1.4 g) and saturated aqueous sodium hydrogen carbonate (15 mL) were added, and the mixture was stirred for 30 min. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was washed with hexane to give tert-butyl 4-{4-[(E)-2-(3-hydroxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-5-methyl-1,3-thiazol-2-yl}piperazine-1-carboxylate (0.97 g, yield 88%) as pale-yellow prism crystals. melting point: 221-223° C.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (15 mL)
  3. additiondi-tert-butyl dicarbonate (1.4 g) and saturated aqueous sodium hydrogen carbonate (15 mL) were added
  4. stirringthe mixture was stirred for 30 min
  5. additionWater was poured into the reaction mixture
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-4312530a7e8e4909aaab292adca4aa82
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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