Benzenesulfonamide → HCID 19780410, compound

HRID 2081703Notes

Reaction equation

HRID 2081703 reaction equation
[CH2:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=1)[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22](O)=[O:23])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)=[O:7])[CH:2]([CH3:4])[CH3:3].[C:28]1([S:34]([NH2:37])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH2:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=1)[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]([NH:37][S:34]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:36])=[O:35])=[O:23])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)=[O:7])[CH:2]([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 7370BenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19780405HCID 19780405, compound

Product 1

HCID 19780410HCID 19780410, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

The carboxylic acid (Example 28 ) (0.25 g) was stirred at room temperature in dichloromethane (3 ml) with benzene sulphonamide (0.10 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.15 g) and 4-dimethylaminopyridine (0.02 g) for 144 hours. The reaction mixture was diluted with chloroform and washed with 0.5N hydrochloric acid, then water. The organic extract was dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo. Purification by preparative reverse-phase HPLC (1 inch LP1-ODS column), eluting with 75:25:0.1 methanol:water:acetic acid, gave N-{1-[3-(isobutoxycarbonylamino)benzyl]indol-5-ylcarbonyl}benzene sulphonamide.

Workup

  1. washwashed with 0.5N hydrochloric acid
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by preparative reverse-phase HPLC (1 inch LP1-ODS column)
  7. washeluting with 75:25:0.1 methanol

Sources & evidence

ORD record
ord-cb54a4a65b524ecfae2b5c631637061d
Source dataset
uspto-grants-1993_02
Patent number
US05185361

Reaction notes

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