Hydrochloric Acid → HCID 178450416, compound

HRID 216392Notes

Reaction equation

HRID 216392 reaction equation
Cl.O1CCOCC1.[F:8][CH:9]([F:56])[C:10]([C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52]([F:55])=[CH:51][N:50]=2)=[CH:45][CH:44]=1)([OH:42])[CH2:11][C:12]1[N:13](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:14]=[C:15]([CH2:17][C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])[N:16]=1>CO>[F:56][CH:9]([F:8])[C:10]([C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52]([F:55])=[CH:51][N:50]=2)=[CH:45][CH:44]=1)([OH:42])[CH2:11][C:12]1[NH:13][CH:14]=[C:15]([CH2:17][C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])[N:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68668071HCID 68668071, compound

Product 1

HCID 178450416HCID 178450416, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

4M Hydrogen chloride in dioxane (1 mL, 0.25 mmol) was added to a solution of 3-(2-{3,3-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-2-hydroxypropyl}-1-trityl-1H-imidazol-4-yl)-2,2-dimethylpropan-1-ol (from previous step) in methanol (1 mL). After stirring at 70° C. for 1 h, volatiles were removed. The residue was basified with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. Combined extracts were dried (magnesium sulfate) and concentrated Chromatography over silica eluting with 0-100% acetone/methylene chloride afforded the title compound. LCMS: 420 (M+H) found.

Workup

  1. customvolatiles were removed
  2. extractionextracted with ethyl acetate
  3. dry with materialCombined extracts were dried (magnesium sulfate)
  4. concentrationconcentrated Chromatography over silica eluting with 0-100% acetone/methylene chloride

Sources & evidence

ORD record
ord-1ec6b431019c477496b1bfa2f058bbe8
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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