Dimethylamine, hydrochloride → 4-[2,6-dichloro-3-[N-methyl-N-[4-(methyl-carbamoyl)cinnamoylglycyl]amino]-benzyloxy]-2-ethyl-1-dimethylcarbamoylmethyl-1H-benzimidazole

HRID 636497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636497
[C:1]([CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([O:14][CH2:15][C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[C:18]([N:23]([CH3:42])[C:24](=[O:41])[CH2:25][NH:26][C:27](=[O:40])[CH:28]=[CH:29][C:30]4[CH:35]=[CH:34][C:33]([C:36](=[O:39])[NH:37][CH3:38])=[CH:32][CH:31]=4)[C:17]=3Cl)[C:8]=2[N:7]=[C:6]1[CH2:44][CH3:45])(O)=[O:2].[ClH:46].[CH3:47][NH:48][CH3:49].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[Cl:46][C:17]1[C:18]([N:23]([CH3:42])[C:24](=[O:41])[CH2:25][NH:26][C:27](=[O:40])[CH:28]=[CH:29][C:30]2[CH:35]=[CH:34][C:33]([C:36](=[O:39])[NH:37][CH3:38])=[CH:32][CH:31]=2)=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=1[CH2:15][O:14][C:13]1[C:8]2[N:7]=[C:6]([CH2:44][CH3:45])[N:5]([CH2:4][C:1](=[O:2])[N:48]([CH3:49])[CH3:47])[C:9]=2[CH:10]=[CH:11][CH:12]=1

Komponenten

7

Edukt 4

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 542002691-carboxymethyl-4-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-2-ethyl-1H-benzimidazole

Produkt 1

HCID 539554454-[2,6-dichloro-3-[N-methyl-N-[4-(methyl-carbamoyl)cinnamoylglycyl]amino]-benzyloxy]-2-ethyl-1-dimethylcarbamoylmethyl-1H-benzimidazoleAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1-carboxymethyl-4-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]-benzyloxy]-2-ethyl-1H-benzimidazole (60 mg), dimethylamine hydrochloride (11.2 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (17.1 mg) and 1-hydroxybenzotriazole (18.6 mg) in dimethylformamide (1 ml) was stirred for 1 day at ambient temperature. To the reaction mixture was added water, and the mixture was extracted with chloroform. The organic layer was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (10% methanol—chloroform) to give 4-[2,6-dichloro-3-[N-methyl-N-[4-(methyl-carbamoyl)cinnamoylglycyl]amino]-benzyloxy]-2-ethyl-1-dimethylcarbamoylmethyl-1H-benzimidazole (46 mg) as amorphous.

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (10% methanol—chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-a544d44396914d8aadbbfa52d4baade5
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194396B1

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