Ammonium Chloride → HCID 178466117, compound

HRID 2244657Notes

Reaction equation

HRID 2244657 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]([C:10]3[N:14]=[C:13]([C:15]4[CH:16]=[CH:17][C:18]([O:23][CH:24]([CH3:29])[C:25]([F:28])([F:27])[F:26])=[C:19]([CH:22]=4)[CH:20]=[O:21])[O:12][N:11]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[BH4-].[Na+].[NH4+].[Cl-:33]>C(O)C>[ClH:33].[NH:3]1[C:4]2[CH:9]=[CH:8][C:7]([C:10]3[N:14]=[C:13]([C:15]4[CH:16]=[CH:17][C:18]([O:23][CH:24]([CH3:29])[C:25]([F:27])([F:28])[F:26])=[C:19]([CH2:20][OH:21])[CH:22]=4)[O:12][N:11]=3)=[CH:6][C:5]=2[N:1]=[CH:2]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 59214390HCID 59214390, compound

Product 1

HCID 178466117HCID 178466117, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-[3-(1H-benzimidazol-6-yl)-1,2,4-oxadiazol-5-yl]-2-(2,2,2-trifluoro-1-methylethoxy)benzaldehyde (80 mg) in ethanol (3 ml) was added NaBH4 (9 mg) at 0° C. After stirring at room temperature for 0.5 hour, a saturated NH4Cl solution (10 ml) was added thereto, followed by extraction with EtOAc (20 ml). The organic layer was washed with saturated brine, dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated. To a solution of the residue (78 mg) in dioxane was added a 4M HCl/dioxane solution, followed by concentration. The resulting powder was recrystallized with IPA (10 ml) to obtain [5-[3-(1H-benzimidazol-5-yl)-1,2,4-oxadiazol-5-yl]-2-(2,2,2-trifluoro-1-methylethoxy)phenyl]methanol hydrochloride (70 mg) as white powders.

Workup

  1. extractionfollowed by extraction with EtOAc (20 ml)
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. additionTo a solution of the residue (78 mg) in dioxane was added a 4M HCl/dioxane solution
  7. concentrationfollowed by concentration
  8. customThe resulting powder was recrystallized with IPA (10 ml)

Sources & evidence

ORD record
ord-43777681fc2849259335494510bb2192
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

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