Dimethylformamide → 7-[(6-Chloropyridin-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamide

HRID 1188880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1188880
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([O:22][C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[CH:13]=[C:14]3[C:18]=2[NH:17][C:16]([C:19](O)=[O:20])=[CH:15]3)[CH:5]=[CH:4][CH:3]=1.Cl.C[N:35](C)CCCN=C=NCC.[NH4+].ON1C2C=CC=CC=2N=N1.CN(C)C=O>O>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([O:22][C:23]3[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=3)[CH:13]=[C:14]3[C:18]=2[NH:17][C:16]([C:19]([NH2:35])=[O:20])=[CH:15]3)[CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 866528367-[(6-Chloropyridin-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylic acid

Produkt 1

HCID 866528377-[(6-Chloropyridin-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 7-[(6-chloropyridin-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylic acid (780 mg), 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (632 mg), 1-hydroxybenzotriazole ammonium salt (502 mg) and N,N-dimethylformamide (30 mL) was stirred at room temperature for 15 hr. Water was added to the reaction solution, and the precipitated solid was collected by filtration, and washed successively with water and diethyl ether to give the title compound (680 mg, yield 90%) as a white solid. The obtained crystals were recrystallized from N,N-dimethylformamide-water to give colorless crystals. melting point 259-260° C.

Aufarbeitung

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed successively with water and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e9ef15e7b14341789bde42c38a9f4eb1
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673942B2

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