Hydrochloric Acid → HCID 178513648, compound

HRID 906180Notes

Reaction equation

HRID 906180 reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9]CC)=[O:8])=[CH:5][C:4]=1[NH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:17][CH2:16]1)#[N:2].OO.C(=O)([O-])[O-:30].[K+].[K+].[OH-].[K+].Cl>CS(C)=O.O.CO>[NH2:2][C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[NH:14][C@H:15]1[CH2:16][CH2:17][C@H:18]([N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[CH2:19][CH2:20]1)=[O:30]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 178468906HCID 178468906, compound

Product 1

HCID 178513648HCID 178513648, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 4-cyano-3-[(trans-4-piperidin-1-ylcyclohexyl)amino]benzoate (0.145 g, 0.41 mmol) in DMSO (0.5 mL) was added a 30% hydrogen peroxide solution (0.078 mL, 0.81 mmol) and potassium carbonate (0.014 g, 0.10 mmol). The reaction mixture was stirred at 50° C. for 3 h. A mixture of methanol (1.5 mL) and water (0.5 mL) was then added followed by potassium hydroxide (0.046 g, 0.81 mmol), and the solution was stirred at 55° C. for 2 h. The mixture was acidified to pH 5 by addition of 1N aqueous hydrochloric acid and lyophilized to afford crude 4-(aminocarbonyl)-3-(trans-4-(piperidin-1-yl)cyclohexylamino]benzoic acid which was used without further purification. MS (EI) for C19H27N3O3: 346 (MH+).

Workup

  1. additionwas then added
  2. stirringthe solution was stirred at 55° C. for 2 h

Sources & evidence

ORD record
ord-154c4b630b4f4276b709dd428779b36f
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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