Hydrochloric Acid → HCID 178513150, compound

HRID 1071783Notes

Reaction equation

HRID 1071783 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:19]1([C:25](Cl)=O)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[Sn](Cl)(Cl)(Cl)Cl.Cl.C(=O)(O)O.[NH2:38][NH:39][C:40]([NH2:42])=[NH:41]>C(Cl)Cl.C(O)(C)C>[CH:19]1([C:25]([C:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])[CH:11]=2)=[N:38][NH:39][C:40](=[NH:41])[NH2:42])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24287Tin tetrachlorideHCID 75938Cyclohexanecarbonyl chlorideHCID 3150171-(Phenylsulfonyl)-1H-indoleHCID 178513185HCID 178513185, compound

Product 1

HCID 178513150HCID 178513150, compoundYield 17.8%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of indole (11.7 g, 0.1 mol) in THF is added to a stirred mixture of NaH (60% dispersion in mineral oil, 4.2, g 0.105 mol), DMSO and THF. The reaction mixture is stirred for 1 h at room temperature, cooled to 0° C., treated with phenylsulfonyl chloride (13.3 mL, 0.15 mol), stirred at ambient temperatures for 3 h, quenched with water and extracted with ethyl acetate. The extracts are combined, dried over MgSO4 and concentrated in vacuo. The resultant residue is crystallized in ethanol and filtered. The filtercake is air-dried to give 1-phenylsulfonylindole. A portion of this 1-phenylsulfonylindole (257 mg, 1.0 mmol) and cyclohexylcarbonyl chloride (0.175 mL, 1.3 mmol) in methylene chloride is treated with tin tetrachloride (97 μL, 1.9 mmol) at room temperature, shaken for 6 h, quenched with saturated NaHCO3 and extracted with ethylacetate. The extracts are combined and concentrated in vacuo to give a residue. The residue is suspended in isopropanol, treated sequentially with concentrated HCl (50 μL) and aminoguanidine bicarbonate (100 mg, 0.5 mmol), heated at 80° C. for 4 h, cooled to room temperature and concentrated in vacuo. The resultant residue is purified by HPLC to afford the title product 37.7 mg (17% yield), identified by HPLC1 and mass spectral analyses.

Workup

  1. customquenched with saturated NaHCO3
  2. extractionextracted with ethylacetate
  3. concentrationconcentrated in vacuo
  4. customto give a residue
  5. temperaturecooled to room temperature
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue is purified by HPLC

Sources & evidence

ORD record
ord-aa7633295bf74becb44e6b69dca966eb
Source dataset
uspto-grants-2005_06
Patent number
US06906095B2

Reaction notes

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