3-Methylpentanoic acid → N-{1-[3-(3-methylbutylcarbonylamino)benzyl]indol-5-ylcarbonyl}-2-methylbenzene sulphonamide

HRID 2081702Notes

Reaction equation

HRID 2081702 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])(=[O:20])=[O:19])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.C[CH:32]([CH2:37][CH3:38])[CH2:33][C:34]([OH:36])=O.Cl.[CH3:40]N(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH3:40][CH:37]([CH3:38])[CH2:32][CH2:33][C:34]([NH:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])(=[O:20])=[O:19])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)=[O:36]

Participants

6

Reactant 3

HCID 77553-Methylpentanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19780416N-[1-(3-aminobenzyl)indol-5-ylcarbonyl]-2-methylbenzene sulphonamide

Product 1

HCID 19780409N-{1-[3-(3-methylbutylcarbonylamino)benzyl]indol-5-ylcarbonyl}-2-methylbenzene sulphonamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of the amine (Example 4) (0.25 g), 3-methylvaleric acid (0.07 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.126 g) and 4-dimethylaminopyridine (0.02 g) in dichloromethane (5 ml) was stirred at room temperature for 96 hours. The reaction mixture was washed with water then saturated brine, dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo. Purification by flash chromatography on silica, eluting with 0-30% ethyl acetate in hexane, afforded N-{1-[3-(3-methylbutylcarbonylamino)benzyl]indol-5-ylcarbonyl}-2-methylbenzene sulphonamide.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialsaturated brine, dried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customPurification by flash chromatography on silica
  6. washeluting with 0-30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-89339267f82641a1807c4b1d82f73b43
Source dataset
uspto-grants-1993_02
Patent number
US05185361

Reaction notes

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