Hydrochloric Acid → HCID 178509279, compound

HRID 59785Notes

Reaction equation

HRID 59785 reaction equation
[NH2:1][C:2]1[NH:3][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([N:13]([CH2:23][C:24]3[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=3[C:26]([O:28]C)=[O:27])[CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH2:9][CH2:8]2)=[N:5][N:6]=1.[OH-].[Na+].Cl>CO>[NH2:1][C:2]1[N:3]=[C:4]([N:7]2[CH2:8][CH2:9][CH:10]([N:13]([CH2:23][C:24]3[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=3[C:26]([OH:28])=[O:27])[CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH2:11][CH2:12]2)[NH:5][N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178497630Methyl 2-(((1-(5-amino-4H-1,2,4-triazol-3-yl)piperidin-4-yl)(4-chlorophenethyl)amino)-methyl)benzoate

Product 1

HCID 178509279HCID 178509279, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(((1-(5-amino-4H-1,2,4-triazol-3-yl)piperidin-4-yl)(4-chlorophenethyl)amino)-methyl)benzoate obtained in Step 3 was dissolved in methanol (10 mL) and 3 mL of 1 N NaOH (aq) was added. The reaction mixture was stirred for 5 hours at room temperature after which time the starting material was no longer present. pH of the reaction mixture was brought to 7 by means of careful addition of 1 N HCl and the solvents were stripped off. The solid residue was passed through the reversed phase C-18 column and the product containing fractions were combined and freeze-dried to give the desired product in a form of white solid (95 mg, 22% yield)

Workup

  1. additionthe product containing fractions
  2. customfreeze-dried

Sources & evidence

ORD record
ord-31a0fb10226e469aad744feb6db5ce4b
Source dataset
uspto-grants-2016_09
Patent number
US09440953B2

Reaction notes

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