Hydrochloric Acid → HCID 178442246, compound

HRID 216418Notes

Reaction equation

HRID 216418 reaction equation
Cl.[F:2][C:3]([F:35])([C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=2)=[CH:24][CH:23]=1)[C:4]([C:6]1[N:7](S(N(C)C)(=O)=O)[CH:8]=[C:9]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[N:10]=1)=[O:5].C[OH:37]>>[CH3:14][C:12]([CH3:13])([CH3:15])[CH2:11][C:9]1[N:10]=[C:6]([C:4]([OH:5])([OH:37])[C:3]([F:2])([F:35])[C:22]2[CH:23]=[CH:24][C:25]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=3)=[CH:26][CH:27]=2)[NH:7][CH:8]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 686681282-{difluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

Product 1

HCID 178442246HCID 178442246, compound

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 2-{difluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-4-(2,2-dimethylpropyl)-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 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 0-50% ethyl acetate/hexane afforded the title compound. LCMS: 406 (M+H).

Workup

  1. customvolatiles were removed
  2. customThe residue was partitioned between 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-8ebdd6c9ad4143af969f5a02a1247eb9
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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