p-Toluenesulfonic acid monohydrate → HCID 67175307, compound

HRID 2362191Notes

Reaction equation

HRID 2362191 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[CH3:11].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=O)[CH2:21][CH2:22][C:23](=O)[CH2:24][CH2:25][C:26](=[O:30])CCC)=[CH:16][CH:15]=1.[OH2:33].[C:34]1([CH3:44])C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:34]([O:33][C:26](=[O:30])[CH2:25][CH2:24][C:23]1[N:1]([C:2]2[CH:10]=[CH:9][C:5]([C:6](=[O:7])[NH2:8])=[CH:4][C:3]=2[CH3:11])[C:20]([C:17]2[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:19][CH:18]=2)=[CH:21][CH:22]=1)[CH3:44]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 121180574-amino-3-methylbenzamideHCID 67175246HCID 67175246, compound

Product 1

HCID 67175307HCID 67175307, compoundYield 301.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-amino-3-methylbenzamide (180 mg, 1.2 mmol) was added to a solution 1-(4-methoxy-phenyl)-decane-1,4,7-trione (350 mg, 1.2 mmol) in ethanol (6 mL), followed by the addition of p-toluenesulfonic acid monohydrate (23 mg, 0.12 mmol). The reaction mixture was heated under reflux for 16 h, and the solvent removed in vacuo to obtain a crude product which upon purification by silica gel flash chromatography, gives 3-[1-(4-carbamoyl-2-methyl-phenyl)-5-(4-methoxy-phenyl)-1H-pyrrol-2-yl]propanoic acid ethyl ester (147 mg, 30%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 16 h
  3. customthe solvent removed in vacuo
  4. customto obtain a crude product which
  5. customupon purification by silica gel flash chromatography

Sources & evidence

ORD record
ord-cdab686e58234a6fbcc7a316ab1999ef
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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