Hydrochloric Acid → HCID 178513151, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])=[CH:5]2.[C:19](Cl)(=O)[CH3:20].[Sn](Cl)(Cl)(Cl)Cl.Cl.C(=O)(O)O.[NH2:33][NH:34][C:35]([NH2:37])=[NH:36]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])=[C:5]2[CH2:20][CH:19]=[N:33][NH:34][C:35](=[NH:36])[NH2:37]Participants
7
Procedure
A solution of 5-chloro-2-(2,4-dichlorophenyl)-1H-indole (160 mg, 0.54 mmol) and acetyl chloride (80 μL, 1.2 mmol) in CH2Cl2 is treated with tin tetrachloride (1.0 M solution in CH2Cl2, 1 mL), shaken at room temperature for 6 h, quenched with saturated NaHCO3 and extracted with ethyl acetate. The extracts are combined and concentrated in vacuo. The resultant residue is suspended in isopropanol and concentrated HCl (100 μL), treated with aminoguanidine bicarbonate (100 mg, 0.75 mmol), heated at 80° C. for 2 h, cooled to room temperature and concentrated in vacuo. This residue is purified by HPLC to afford the title compound, 7.0 mg (3% yield), identified by HPLC1 and mass spectral analyses; (M+H) 395; retention time 4.51 min.
Workup
- customquenched with saturated NaHCO3
- extractionextracted with ethyl acetate
- concentrationconcentrated in vacuo
- temperatureheated at 80° C. for 2 h
- temperaturecooled to room temperature
- concentrationconcentrated in vacuo
- customThis residue is purified by HPLC
Sources & evidence
- ORD record
- ord-a76bed57e44046ebb6cc9e7ebb2c6d4f
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06951881B2
Reaction notes
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