Hydrochloric Acid → Da-6886

HRID 1506936Notes

Reaction equation

HRID 1506936 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5](C(N)=O)=[C:4]([O:12][CH3:13])[C:3]=1CC1CCNCC1.Cl.CS(O[CH2:27][CH2:28][CH2:29][N:30]1[CH:34]=[CH:33][N:32]=[N:31]1)(=O)=O.C([N:37]([CH2:40][CH3:41])[CH2:38][CH3:39])C.[C:42](=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:50][N:51](C)[CH:52]=[O:53]>>[N:30]1([CH2:29][CH2:28][CH2:27][N:37]2[CH2:38][CH2:39][CH:42]([CH2:50][NH:51][C:52](=[O:53])[C:5]3[CH:9]=[C:10]([Cl:11])[C:2]([NH2:1])=[CH:3][C:4]=3[O:12][CH3:13])[CH2:41][CH2:40]2)[CH:34]=[CH:33][N:32]=[N:31]1

Participants

8

Reactant 7

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 6228DimethylformamideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 866805484-Amino-5-chloro-2-methoxy-(piperidin-4-ylmethyl) benzamide2×HCID 866805493-(1,2,3-Triazol-1-yl)propyl methanesulfonate2×

Product 1

HCID 54575171Da-6886Yield 38%

Conditions

Temperature
120 °C

Procedure

4-amino-5-chloro-2-methoxy-(piperidin-4-ylmethyl)benzamide (compound of formula 2) hydrochloride (400 mg, 1.2 mmol) was dissolved in dimethylformamide (10 mL), and 3-(1,2,3-triazol-1-yl)propyl methanesulfonate (compound of formula 3) (344 mg, 1.68 mmol), triethylamine (0.5 mL, 3.591 mmol), potassium carbonate (232 mg, 1.68 mmol), and potassium iodide (40 mg, 0.24 mmol) were added thereto, followed by stirring at 120° C. for 4 hours. After the reaction was completed, the reactants were cooled to room temperature, extracted with ethyl acetate and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography to afford the title compound (185 mg, 38%).

Workup

  1. temperaturethe reactants were cooled to room temperature
  2. extractionextracted with ethyl acetate and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-a4574c81ae6b45b2bf0de9ec33dfeb9c
Source dataset
uspto-grants-2015_12
Patent number
US09221790B2

Reaction notes

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