Benzenesulfonyl chloride, 3,4-dichloro- → HCID 58499381, compound

HRID 910273Notes

Reaction equation

HRID 910273 reaction equation
[NH2:1][C@@H:2]([C:4]1[N:5]([CH2:25][CH3:26])[C:6]([O:9][C:10]2[CH:11]=[C:12]([N:16]3[CH2:21][CH2:20][N:19]([C:22](=[O:24])[CH3:23])[CH2:18][CH2:17]3)[CH:13]=[CH:14][CH:15]=2)=[N:7][N:8]=1)[CH3:3].Cl.C(N(CC)CC)C.[Cl:35][C:36]1[CH:37]=[C:38]([S:43](Cl)(=[O:45])=[O:44])[CH:39]=[CH:40][C:41]=1[Cl:42].C([O-])([O-])=O.[K+].[K+]>O>[C:22]([N:19]1[CH2:18][CH2:17][N:16]([C:12]2[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=2)[O:9][C:6]2[N:5]([CH2:25][CH3:26])[C:4]([C@H:2]([NH:1][S:43]([C:38]3[CH:39]=[CH:40][C:41]([Cl:42])=[C:36]([Cl:35])[CH:37]=3)(=[O:45])=[O:44])[CH3:3])=[N:8][N:7]=2)[CH2:21][CH2:20]1)(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 11130Triethylamine hydrochlorideHCID 11430Potassium CarbonateHCID 58499358HCID 58499358, compound

Product 1

HCID 58499381HCID 58499381, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Water was added to a mixture (307 mg) of 1-(4-[3-[5-((R)-1-aminoethyl)-4-ethyl-4H-[1,2,4]triazol-3-yloxy]-phenyl]-piperazin-1-yl)-ethanone obtained in Example 27-(2) and triethylamine hydrochloride, 3,4-dichlorobenzenesulfonyl chloride (0.13 ml), and K2CO3 (355 mg). The mixture was stirred at room temperature for 15 hours. The precipitated solid was filtered and purified by column chromatography (NH SiO2, MeOH/CHCl3=1/50) to give the titled compound (Compound 697) (117 mg, colorless syrup).

Workup

  1. filtrationThe precipitated solid was filtered
  2. custompurified by column chromatography (NH SiO2, MeOH/CHCl3=1/50)

Sources & evidence

ORD record
ord-8c22aa5768b74f389334683eb42326b7
Source dataset
uspto-grants-2011_09
Patent number
US08022091B2

Reaction notes

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