Benzenesulfonyl chloride → HCID 178493140, compound

HRID 722047Notes

Reaction equation

HRID 722047 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([CH2:19][CH2:20][C:21]2[NH:36][C:24]3=[N:25][CH:26]=[C:27]([C:29]4[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=4)[CH:28]=[C:23]3[N:22]=2)[CH:14]=1>N1C=CC=CC=1>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([CH2:19][CH2:20][C:21]2[NH:36][C:24]3=[N:25][CH:26]=[C:27]([C:29]4[CH:34]=[CH:33][C:32]([NH:35][S:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)(=[O:9])=[O:8])=[CH:31][CH:30]=4)[CH:28]=[C:23]3[N:22]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 178493138HCID 178493138, compound

Product 1

HCID 178493140HCID 178493140, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.047 ml of benzene sulfonyl chloride are added to 0.115 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-(4-aminophenyl)-3H-imidazo[4,5-b]pyridine (example 27) in 1 ml of pyridine and the mixture is stirred at ambient temperature for three hours. The solvent is evaporated in vacuo and the residue is is chromatographed on a silica gel column (dichloromethane/methanol 30–20:1+1% triethylamine). Concentration of the chromatographically pure fractions and drying gives 0.093 g of the title compound as a solid of m.p. 251–253° C. The mass spectrum shows the molecular peak MH+ at 486.3 Da.

Workup

  1. customThe solvent is evaporated in vacuo
  2. customthe residue is is chromatographed on a silica gel column (dichloromethane/methanol 30–20:1+1% triethylamine)
  3. customConcentration of the chromatographically pure fractions and drying

Sources & evidence

ORD record
ord-9b36baea5d3044ebb9e7251fc4576cea
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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