Hydrochloric Acid → HCID 68819211, compound

HRID 1818744Notes

Reaction equation

HRID 1818744 reaction equation
[F:1][C:2]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2COCC[Si](C)(C)C)=[C:7]([O:22][CH2:23][CH:24]2[CH2:28][O:27]C(C)(C)[O:25]2)[CH:6]=1.O.Cl>CO>[F:1][C:2]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][NH:11]2)=[C:7]([O:22][CH2:23][CH:24]([OH:25])[CH2:28][OH:27])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68818478HCID 68818478, compound

Product 1

HCID 68819211HCID 68819211, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

6-(2,4-Difluoro-phenoxy)-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (0.905 g, 1.79 mmol) was dissolved in 20 mL of MeOH. Water (12 mL) and concentrated HCl (12 mL) were added, and the reaction mixture was sealed and heated to 90° C. for 30 minutes. The reaction mixture was cooled and concentrated under reduced pressure, and the residue was taken up in MeOH, made pH neutral by dropwise addition of aqueous NH4OH solution, and concentrated to dryness under reduced pressure. The residue was chromatographed through silica (0%-1 0% EtOAc in hexanes) to give 0.522 g of 3-[6-(2,4-difluoro-phenoxy)-1H-indazol-4-yloxy]-propane-1,2-diol, MS(M+H)=337.

Workup

  1. customthe reaction mixture was sealed
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. additionneutral by dropwise addition of aqueous NH4OH solution
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue was chromatographed through silica (0%-1 0% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4bfd1b61cccd433ebc2eb1f0fddf3842
Source dataset
uspto-grants-2009_10
Patent number
US07601726B2

Reaction notes

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