p-Anisoyl chloride → N-{2-[4-(5-isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-4-methoxy-benzamide

HRID 2266400Notes

Reaction equation

HRID 2266400 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.Cl.[NH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26]2[S:27][C:28]([CH:31]([CH3:33])[CH3:32])=[N:29][N:30]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1>ClCCl>[CH:31]([C:28]1[S:27][C:26]([NH:25][S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][NH:13][C:7](=[O:8])[C:6]3[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[CH:17][CH:18]=2)(=[O:24])=[O:23])=[N:30][N:29]=1)([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 687820324-(2-Amino-ethyl)-N-(5-isopropyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide hydrochloride

Product 1

HCID 57586819N-{2-[4-(5-isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-4-methoxy-benzamideYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

21.4 mg 4-Methoxy-benzoyl chloride and 50 mg 4-(2-Amino-ethyl)-N-(5-isopropyl-[1,3,4]thiadiazol-2-yl)-benzene sulfonamide hydrochloride were dissolved in 2 ml dichloromethane and stirred at room temperature for two hours. The reaction mixture was diluted by addition of 50 ml dichloromethane, washed three times with portions of 30 ml water and then dried over MgSO4. The solvent was removed in vacuo. The residue was purified by RP-HPLC to obtain 21.4 mg N-{2-[4-(5-isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-4-methoxy-benzamide.

Workup

  1. washwashed three times with portions of 30 ml water
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-29f13bf61ff3475e91fab187d5417cd1
Source dataset
uspto-grants-2010_12
Patent number
US07858647B2

Reaction notes

Loading…