Hydrochloric Acid → HCID 25020358, compound

HRID 561244Notes

Reaction equation

HRID 561244 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:42])[N:10]([CH2:34][CH:35](OCC)OCC)[C:11]2[CH:12]=[N:13][N:14]([C@@H:16]([C@:18]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[F:33])([OH:25])[CH2:19][N:20]3[CH:24]=[N:23][CH:22]=[N:21]3)[CH3:17])[CH:15]=2)=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:35]=[CH:34][N:10]([C:11]3[CH:12]=[N:13][N:14]([C@@H:16]([C@:18]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=4[F:33])([OH:25])[CH2:19][N:20]4[CH:24]=[N:23][CH:22]=[N:21]4)[CH3:17])[CH:15]=3)[C:9]2=[O:42])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 25020302HCID 25020302, compound

Product 1

HCID 25020358HCID 25020358, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(4-Chlorophenyl)-1-(2,2-diethoxyethyl)-1-(1-((2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl)-1H-pyrazol-4-yl)urea obtained in Step 4 (0.07 g, 0.12 mmol) was dissolved in methanol (2 mL) and 1N-HCl (2 mL) was added thereto. The mixture was refluxed for 2 hours, and neutralized using aqueous sodium hydrogen carbonate. The resulting mixture was extracted with ethyl acetate (10 mL), and the extract was washed successively with distilled water (10 mL) and brine (10 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated by evaporation under a reduced pressure. The resulting residue was purified by silica gel chromatography to obtain the title compound (0.056 g, yield 95%).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. extractionThe resulting mixture was extracted with ethyl acetate (10 mL)
  3. washthe extract was washed successively with distilled water (10 mL) and brine (10 mL)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under a reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f21d293d55e046f8857cd6f4934df946
Source dataset
uspto-grants-2011_11
Patent number
US08063229B2

Reaction notes

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