Hydrochloric Acid → HCID 178442234, compound

HRID 425352Notes

Reaction equation

HRID 425352 reaction equation
Cl.[CH3:2][C:3]([CH3:35])([CH3:34])[CH2:4][C:5]1[N:6]=[C:7]([C:16]([OH:33])([CH3:32])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][N:25]=3)=[CH:20][C:19]=2[F:31])[N:8](S(N(C)C)(=O)=O)[CH:9]=1>CO>[CH3:2][C:3]([CH3:35])([CH3:34])[CH2:4][C:5]1[N:6]=[C:7]([C:16]([OH:33])([CH3:32])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][N:25]=3)=[CH:20][C:19]=2[F:31])[NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66705639HCID 66705639, compound

Product 1

HCID 178442234HCID 178442234, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Hydrogen chloride (4 M in 1,4-dioxane) (1 mL, 4 mmol) was added to an ambient temperature solution of 4-(2,2-dimethylpropyl)-2-{2-[2-fluoro-4-(5-fluoropyridin-2-yl)phenyl]-1-hydroxy-1-methylethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide (20 mg, 0.04 mmol) in methanol (2 mL). After stirring at 70° C. for 1 h, volatiles were removed. The residue was partitioned between methanol/ethyl acetate and 10% aqueous sodium hydroxide. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% acetone/methylene chloride then with 0-100% acetone/methylene chloride afforded the title compound. (M+H) found: 386.

Workup

  1. customvolatiles were removed
  2. customThe residue was partitioned between methanol/ethyl acetate and 10% aqueous sodium hydroxide
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50a69cd699b8426e82b4fb54983e8a37
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

Loading…