Benzenesulfonyl chloride, 3,4-dichloro- → HCID 21865603, compound

HRID 857294Notes

Reaction equation

HRID 857294 reaction equation
[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([CH:24]([N:26]([C:35]4[CH:40]=[CH:39][C:38]([S:41]([CH3:44])(=O)=O)=[CH:37][CH:36]=4)C(=O)C4C=CC=CC=4)[CH3:25])[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:4])=[O:3].[Cl:45][C:46]1[CH:47]=[C:48]([S:53](Cl)(=[O:55])=[O:54])[CH:49]=[CH:50][C:51]=1[Cl:52]>N1C=CC=CC=1.C([O-])(O)=O.[Na+]>[Cl:45][C:46]1[CH:47]=[C:48]([S:53]([N:26]([CH:24]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:16]3[CH:17]=[C:8]([C:5]([S:2]([CH3:1])(=[O:4])=[O:3])([CH3:7])[CH3:6])[CH:9]=[C:10]4[C:15]=3[N:14]=[CH:13][CH:12]=[CH:11]4)[CH:19]=2)[CH3:25])[C:35]2[CH:36]=[CH:37][C:38]([S:41][CH3:44])=[CH:39][CH:40]=2)(=[O:55])=[O:54])[CH:49]=[CH:50][C:51]=1[Cl:52]

Participants

5

Reactant 2

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 10312400HCID 10312400, compound

Product 1

HCID 21865603HCID 21865603, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

To solution of (1-{3-[6-(1-Methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-phenyl}-ethyl)-(4-methylsulfanyl-phenyl)-amine from EXAMPLE 44 (Step 1) (1.0 eq) in pyridine (0.38M) was added 3,4-dichloro-benzenesulfonyl chloride (3.2 eq). The resulting mixture was stirred at 80° C. for 12 h, cooled to room temperature, poured in saturated aqueous NaHCO3 and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (CH2Cl2:EtOAc; 9:1) afforded the desired compound as a foam.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aeb76cbf79224eaa93eb5cdfd82ac7cc
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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