2-Methylbenzenesulfonamide → N-[4-[1-(2-Carbamoylethyl)-5-(N-cyclopentylmethyl carbamoyl)indol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamide

HRID 728680Notes

Reaction equation

HRID 728680 reaction equation
[C:1]([CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15](=[O:23])[NH:16][CH2:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:12][CH:13]=2)[C:8]([CH2:24][C:25]2[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][C:26]=2[O:34][CH3:35])=[CH:7]1)(=[O:3])[NH2:2].Cl.CN(C)CCCN=C=NCC.[C:48]1([CH3:58])[C:49]([S:54]([NH2:57])(=[O:56])=[O:55])=[CH:50][CH:51]=[CH:52][CH:53]=1>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15](=[O:23])[NH:16][CH2:17][CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)=[CH:12][CH:13]=2)[C:8]([CH2:24][C:25]2[CH:33]=[CH:32][C:28]([C:29]([NH:57][S:54]([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=3[CH3:58])(=[O:55])=[O:56])=[O:30])=[CH:27][C:26]=2[O:34][CH3:35])=[CH:7]1)(=[O:3])[NH2:2]

Participants

6

Reactant 3

HCID 69242-MethylbenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 198224694[1-(2-Carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indol-3-ylmethyl]-3-methoxybenzoic acid

Product 1

HCID 19822468N-[4-[1-(2-Carbamoylethyl)-5-(N-cyclopentylmethyl carbamoyl)indol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamideYield 37%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-[1-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indol-3-ylmethyl]-3-methoxybenzoic acid (77 mg), 4-(dimethylamino)pyridine (20 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (37 mg), and ortho-toluenesulphonamide (28 mg) in dichloromethane (2.0 ml) was stirred under a nitrogen atmosphere for 48 hours. The mixture was diluted with dichloromethane; washed with 10% v/v hydrochloric acid, water, and brine; and evaporated. The resulting white solid was crystallized from ethyl acetate/hexane to give the title compound (37 mg; 37%) as a white solid; mp 140°-145° C. (d).

Workup

  1. washwashed with 10% v/v hydrochloric acid, water, and brine
  2. customand evaporated
  3. customThe resulting white solid was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a4a8d98edf6047ff90f803fa360574cd
Source dataset
uspto-grants-1991_09
Patent number
US05049679

Reaction notes

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