Hydrochloric Acid → N-((1-(3-(1,2,4-triazol-1-yl)propyl)piperidin-4-yl)methyl)-4-amino-5-chloro-2-methoxybenzamide

HRID 1506933Notes

Reaction equation

HRID 1506933 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([O:12][CH3:13])[C:3]=1CC1CCNCC1.Cl.Cl[CH2:23][CH2:24][CH2:25][N:26]1[CH:30]=[N:29][CH:28]=[N:27]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:39][N:40]([CH3:43])C=O>>[N:26]1([CH2:25][CH2:24][CH2:23][N:40]2[CH2:43][CH2:6][CH:5]([CH2:9][NH:8][C:6](=[O:7])[C:5]3[CH:9]=[C:10]([Cl:11])[C:2]([NH2:1])=[CH:3][C:4]=3[O:12][CH3:13])[CH2:4][CH2:39]2)[CH:30]=[N:29][CH:28]=[N:27]1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 167906881-(3-chloropropyl)-1H-1,2,4-triazole2×HCID 866805484-Amino-5-chloro-2-methoxy-(piperidin-4-ylmethyl) benzamide2×

Product 1

HCID 66780300N-((1-(3-(1,2,4-triazol-1-yl)propyl)piperidin-4-yl)methyl)-4-amino-5-chloro-2-methoxybenzamideYield 9%

Conditions

Temperature
100 °C

Procedure

4-amino-5-chloro-2-methoxy-(piperidin-4-ylmethyl)benzamide (compound of formula 2) hydrochloride (500 mg, 1.5 mmol) was dissolved in dimethylformamide (10 mL), and 1-(3-chloropropyl)-1,2,4-triazole (compound of formula 3) (306 mg, 2.1 mmol), potassium carbonate (497 mg, 3.6 mmol), and potassium iodide (50 mg, 0.3 mmol) were added thereto. The reactants were stirred at 100° C. for 8 hours, and the reaction was terminated with the addition of water. After extraction with ethyl acetate and water, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography to afford the title compound (55 mg, 9%).

Workup

  1. customthe reaction was terminated with the addition of water
  2. extractionAfter extraction with ethyl acetate and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-1ea90f85299341b48a0594bc2d3b7981
Source dataset
uspto-grants-2015_12
Patent number
US09221790B2

Reaction notes

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