2-Methylbenzenesulfonamide → N-[4-[6-(N-Cyclopentylmethylcarbamoyl)-3-[2-(N-methylcarbamoyl)ethyl]indol-1-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamide

HRID 1198964Notes

Reaction equation

HRID 1198964 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH2:31][CH2:32][C:33](=[O:36])[NH:34][CH3:35])=[CH:15][N:16]3[CH2:19][C:20]3[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][C:21]=3[O:29][CH3:30])=[CH:12][CH:11]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.CN(C)CCCN=C=NCC.[C:49]1([CH3:59])[C:50]([S:55]([NH2:58])(=[O:57])=[O:56])=[CH:51][CH:52]=[CH:53][CH:54]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH2:31][CH2:32][C:33](=[O:36])[NH:34][CH3:35])=[CH:15][N:16]3[CH2:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH:58][S:55]([C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=4[CH3:59])(=[O:57])=[O:56])=[O:25])=[CH:22][C:21]=3[O:29][CH3:30])=[CH:12][CH:11]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 69242-MethylbenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 150137804-[6-(N-cyclopentylmethylcarbamoyl)-3-[2-(N-methylcarbamoyl)ethyl]indol-1-ylmethyl]-3-methoxybenzoic acid

Product 1

HCID 15013783N-[4-[6-(N-Cyclopentylmethylcarbamoyl)-3-[2-(N-methylcarbamoyl)ethyl]indol-1-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamideYield 18.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-[6-(N-cyclopentylmethylcarbamoyl)-3-[2-(N-methylcarbamoyl)ethyl]indol-1-ylmethyl]-3-methoxybenzoic acid (0.25 g) (prepared as described in Example 1), 4-(dimethylamino)pyridine (0.07 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.12 g), and ortho-toluenesulphonamide (0.09 g) in methylene chloride (3.0 ml) was stirred under a nitrogen atmosphere for 24 hours. The mixture was diluted with methylene chloride, washed sequentially with 10% (v/v) hydrochloric acid, water, and brine, and evaporated. The resulting ivory solid was purified by flash chromatography on silica gel (10 ml), eluting with 1:9 methanol:chloroform, to give the title compound (0.06 g, 17%) as an ivory powder; mp 211°-212°.

Workup

  1. washwashed sequentially with 10% (v/v) hydrochloric acid, water, and brine
  2. customevaporated
  3. customThe resulting ivory solid was purified by flash chromatography on silica gel (10 ml)
  4. washeluting with 1:9 methanol

Sources & evidence

ORD record
ord-4dd2038cae544d2da58ee9504993e324
Source dataset
uspto-grants-1990_02
Patent number
US04898863

Reaction notes

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