Ammonium Chloride → HCID 58546931, compound

HRID 1850329Notes

Reaction equation

HRID 1850329 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:15][CH:14]([C:16]2[C:17]([C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[CH:24][CH:23]=3)=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:13]1)=[O:11].[BH4-].[BH4-].[BH4-].[BH4-].[Na+].[Na+].[Na+].[Na+].[Cl-].[NH4+]>CO>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:13][CH:14]([C:16]2[C:17]([C:22]3[CH:23]=[CH:24][C:25]([CH:28]([OH:30])[CH3:29])=[CH:26][CH:27]=3)=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:15]1)=[O:11]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 58546981HCID 58546981, compoundHCID 131720822Sodium tetraborohydride

Product 1

HCID 58546931HCID 58546931, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-{3-[1-(1H-benzoimidazole-2-carbonyl)-azetidin-3-yl]-pyrazin-2-yl}-phenyl)-ethanone (100 mg, 0.25 mmol, Scheme 2, Example 2.21) was dissolved in 10 ml of methanol. This solution was cooled down to 0° C. using an ice bath and sodium tetraborohydride (19 mg, 0.50 mmol) was added by portions. The reaction mixture was stirred for 4 h at ambient temperature, then saturated aqueous solution of ammonium chloride (5 mL) was added. The methanol was evaporated off under reduced pressure then the reaction mixture was taken up in ethyl acetate. The organic phase was separated from the aqueous phase. This extraction was repeated one more time and then the organic phases were combined and dried over magnesium sulphate, followed by concentrating under reduced pressure. The residue was purified by column chromatography to give the title compound (75 mg, 0.19 mmol, 75% yield).

Workup

  1. customThe methanol was evaporated off under reduced pressure
  2. customThe organic phase was separated from the aqueous phase
  3. extractionThis extraction
  4. dry with materialdried over magnesium sulphate
  5. concentrationby concentrating under reduced pressure
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8c8033b0c7bc4c449184a9608e95d0fd
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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