Aniline → HCID 86710121, compound
Reaction equation
[CH:1]([C:4]1[N:5]=[C:6]2[CH:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[CH:8][N:7]2[C:15]=1[S:16]([OH:19])(=[O:18])=O)([CH3:3])[CH3:2].C(N(CC)CC)C.P(Cl)(Cl)([Cl:29])=O.[NH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])O.[Na+]>ClC(Cl)C>[CH:1]([C:4]1[N:5]=[C:6]2[CH:11]=[C:10]([C:12](=[O:14])[NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:9]=[CH:8][N:7]2[C:15]=1[S:16]([Cl:29])(=[O:18])=[O:19])([CH3:2])[CH3:3]Participants
Conditions
- Temperature
- 100 °C
Procedure
2-Isopropyl-3-sulfoimidazo[1,2-a]pyridine-7-carboxylic acid (0.93 g, 3.25 mmol) obtained in step 2 was dissolved in dichloroethane (30 mL), and the solution was stirred at 100° C. for 4 hours after adding triethylamine (1.13 mL, 8.13 mmol) and phosphorus oxychloride (0.760 mL, 8.13 mmol). The reaction mixture was allowed to cool to room temperature, and stirred at room temperature for 2.5 hours after adding aniline (0.300 mL, 3.25 mmol). Then, a saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→50/50) to give 2-isopropyl-7-phenylcarbamoylimidazo[1,2-a]pyridine-3-sulfonylchloride (1.24 g, yield 97%).
Workup
- temperatureto cool to room temperature
- stirringstirred at room temperature for 2.5 hours
- extractionthe mixture was extracted with chloroform
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- customthe solvent was then evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→50/50)
Sources & evidence
- ORD record
- ord-2602bc69a4974ac5bc0e24f517e3734e
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09000186B2
Reaction notes
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