1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-[3-(4,5-dimethyl-imidazol-1-yl)-phenyl]-2,3-dimethyl-1H-indole-7-carboxamide

HRID 1835485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1835485
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=2[C:12]([OH:14])=O.[CH3:15][C:16]1[N:17]=[CH:18][N:19]([C:22]2[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=2)[NH2:25])[C:20]=1[CH3:21].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:15][C:16]1[N:17]=[CH:18][N:19]([C:22]2[CH:23]=[C:24]([NH:25][C:12]([C:5]3[CH:6]=[CH:7][CH:8]=[C:9]4[C:4]=3[NH:3][C:2]([CH3:1])=[C:10]4[CH3:11])=[O:14])[CH:26]=[CH:27][CH:28]=2)[C:20]=1[CH3:21]

Komponenten

6

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 37026102,3-Dimethyl-7-indolecarboxylic acidHCID 235036513-(4,5-Dimethylimidazol-1-yl)phenylamine

Produkt 1

HCID 23503675N-[3-(4,5-dimethyl-imidazol-1-yl)-phenyl]-2,3-dimethyl-1H-indole-7-carboxamideAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of 2,3-dimethyl-1H-indole-7-carboxylic acid (95 mg) and 3-(4,5-dimethylimidazol-1-yl)aniline (94 mg) in dichloromethane (2 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (135 mg) and 4-dimethylaminopyridine (31 mg), and the mixture was stirred for 12 hours. The mixture was diluted with dichloromethane and washed with water and brine. The mixture was dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with dichloromethane, and the insoluble material was collected by filtration and dried to give N-[3-(4,5-dimethyl-imidazol-1-yl)-phenyl]-2,3-dimethyl-1H-indole-7-carboxamide (77 mg, 43.0%).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe mixture was dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was triturated with dichloromethane
  5. filtrationthe insoluble material was collected by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9b84452f0e68430fa155b295dc065b3b
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06770667B1

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