Ammonium Chloride → 1-(1-(3-((1-(Quinolin-2-yl)azetidin-3-yl)oxy)pyrazin-2-yl)piperidin-4-yl)ethanol

HRID 2207818Notes

Reaction equation

HRID 2207818 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([O:15][C:16]2[C:17]([N:22]3[CH2:27][CH2:26][CH:25]([C:28](=[O:30])[CH3:29])[CH2:24][CH2:23]3)=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:12]1.[BH4-].[BH4-].[BH4-].[BH4-].[Na+].[Na+].[Na+].[Na+].[Cl-].[NH4+]>CO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([O:15][C:16]2[C:17]([N:22]3[CH2:27][CH2:26][CH:25]([CH:28]([OH:30])[CH3:29])[CH2:24][CH2:23]3)=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 585478461-(1-(3-((1-(Quinolin-2-YL)azetidin-3-YL)oxy)pyrazin-2-YL)piperidin-4-YL)ethanoneHCID 131720822Sodium tetraborohydride

Product 1

HCID 585478761-(1-(3-((1-(Quinolin-2-yl)azetidin-3-yl)oxy)pyrazin-2-yl)piperidin-4-yl)ethanolYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1-(1-(3-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyrazin-2-yl)piperidin-4-yl)ethanone (100 mg, 0.25 mmol) 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 in portions. The reaction mixture was stirred for 4 hours at ambient temperature, and 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 layer was separated from the aqueous layer. This extraction was repeated one more time and then the organic layers were combined and dried over magnesium sulphate, followed by concentrating under reduced pressure. The residue was purified by column chromatography on silica gel to give (racemic mixture) 1-(1-(3-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyrazin-2-yl)piperidin-4-yl)ethanol (75 mg, 0.19 mmol, 75% yield). ESI-MS (M+1): 406 calc. for C23H27N5O2 405.

Workup

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

Sources & evidence

ORD record
ord-c2a71e4b54c74edaa6edfa8bf43f32aa
Source dataset
uspto-grants-2016_06
Patent number
US09376450B2

Reaction notes

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