Benzenesulfonyl chloride → N-[2-((S)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl]-benzenesulfonamide

HRID 496414Notes

Reaction equation

HRID 496414 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[C:14]([O:15][C@@H:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][C:10]2=[O:29].[C:30]1([S:36](Cl)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[N:18]1([CH2:17][C@H:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[O:15][C:14]2[CH:13]=[CH:12][C:11]3[C:10](=[O:29])[CH2:9][CH2:8][CH2:7][C:6]=3[C:5]=2[CH2:4][NH:3][S:36]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(=[O:38])=[O:37])[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 208287285-aminomethyl-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one bis-hydrochloride

Product 1

HCID 60029894N-[2-((S)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl]-benzenesulfonamideYield 67%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

5-Aminomethyl-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one bis-hydrochloride (74 mg, 0.171 mmol) was dissolved in pyridine (1 mL) and catalytic DMAP (2 mg) was added followed by benzenesulfonyl chloride (26 μL, 0.205 mmol, 1.2 equiv). The reaction was stirred overnight at RT. The mixture was concentrated and the residue was dissolved in CH2Cl2. The organics were washed with H2O and brine, dried over MgSO4 and concentrated to give a tan foam. Purification by chromatography (5% MeOH/EtOAc with 1% NH4OH) afforded the title compound as a white foam (57 mg, 0.114 mmol, 67%). The structure was confirmed by NMR and mass spectrometry. MS m/z 502 (M++H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washThe organics were washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a tan foam
  7. customPurification by chromatography (5% MeOH/EtOAc with 1% NH4OH)

Sources & evidence

ORD record
ord-520a6fc8266f4ee180aa1738e059e3fb
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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