Hydrochloric Acid → HCID 178441352, compound

HRID 216393Notes

Reaction equation

HRID 216393 reaction equation
Cl.O1CCOCC1.[F:8][CH:9]([F:60])[C:10]([C:47]1[CH:52]=[CH:51][C:50]([C:53]2[CH:58]=[CH:57][C:56]([F:59])=[CH:55][N:54]=2)=[CH:49][CH:48]=1)([OH:46])[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]([CH3:26])([CH3:25])[CH:19]([OH:24])[C:20]([F:23])([F:22])[F:21])[N:16]=1.FC(F)C(C1C=CC(C2C=CC(F)=CN=2)=CC=1)(O)CC1N(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=C(CC(C)(C)C(O[Si](C)(C)C)C(F)(F)F)N=1>CO>[F:60][CH:9]([F:8])[C:10]([C:47]1[CH:48]=[CH:49][C:50]([C:53]2[CH:58]=[CH:57][C:56]([F:59])=[CH:55][N:54]=2)=[CH:51][CH:52]=1)([OH:46])[CH2:11][C:12]1[NH:13][CH:14]=[C:15]([CH2:17][C:18]([CH3:25])([CH3:26])[CH:19]([OH:24])[C:20]([F:22])([F:23])[F:21])[N:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86638505HCID 86638505, compoundHCID 86638506HCID 86638506, compound

Product 1

HCID 178441352HCID 178441352, 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 4-(2-{3,3-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-2-hydroxypropyl}-1-trityl-1H-imidazol-4-yl)-1,1,1-trifluoro-3,3-dimethylbutan-2-ol and 1,1-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-3-(4-{4,4,4-trifluoro-2,2-dimethyl-3-[(trimethylsilyl)oxy]butyl}-1-trityl-1H-imidazol-2-yl)propan-2-ol (from previous step) in methanol (2 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 0-60% acetone/methylene chloride afforded the title compound. LCMS: 488 (M+H).

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 0-60% acetone/methylene chloride

Sources & evidence

ORD record
ord-cde87589f3414cbb88dc1f88a2126a76
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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