2-Methylbenzenesulfonamide → HCID 14882515, compound

HRID 330143Notes

Reaction equation

HRID 330143 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]([CH2:10][C:11]2[CH:19]=[C:18]3[C:14]([CH:15]=[CH:16][N:17]3[CH2:20][C:21]3[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][C:22]=3[O:30][CH3:31])=[CH:13][CH:12]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.CN(C)CCCN=C=NCC.[CH3:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[S:51]([NH2:54])(=[O:53])=[O:52]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:1]1([CH2:6][NH:7][C:8]([CH2:10][C:11]2[CH:19]=[C:18]3[C:14]([CH:15]=[CH:16][N:17]3[CH2:20][C:21]3[CH:29]=[CH:28][C:24]([C:25]([NH:54][S:51]([C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=4[CH3:44])(=[O:53])=[O:52])=[O:26])=[CH:23][C:22]=3[O:30][CH3:31])=[CH:13][CH:12]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 69242-MethylbenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14882506HCID 14882506, compound

Product 1

HCID 14882515HCID 14882515, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-[6-(cyclopentylmethylcarbamoyl)methylindol-1-ylmethyl]-3-methoxybenzoic acid (0.60 g), 4-dimethylaminopyridine (0.18 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.33 g), and 2-methylbenzenesulfonamide (0.25 g) in methylene chloride (70 ml) was stirred under a nitrogen atmosphere for 80 hr. The mixture was diluted with methylene chloride, washed with 10% v/v hydrochloric acid and water, and evaporated. The resulting white solid was precipitated from methylene chloride with hexane to give the title compound (0.62 g, 76%) as a white solid: mp 187°-188°.

Workup

  1. washwashed with 10% v/v hydrochloric acid and water
  2. customevaporated
  3. customThe resulting white solid was precipitated from methylene chloride with hexane

Sources & evidence

ORD record
ord-e6a4fc0289c746a1a8ebcdd7c093430c
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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