1,2-Dichloroethane → N-[4-({2-[(4-chlorophenyl)amino]-1-methyl-1H-benzimidazol-5-yl}oxy)pyridin-2-yl]benzamide

HRID 30791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30791
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:26]=[CH:25][C:12]3[N:13]([CH3:24])[C:14]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=4)=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[C:41](O)(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>O1CCCC1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:14]2[N:13]([CH3:24])[C:12]3[CH:25]=[CH:26][C:9]([O:8][C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:41](=[O:48])[C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[CH:7]=4)=[CH:10][C:11]=3[N:15]=2)=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 181649HOAtHCID 69290969HCID 69290969, Verbindung

Produkt 1

HCID 59790184N-[4-({2-[(4-chlorophenyl)amino]-1-methyl-1H-benzimidazol-5-yl}oxy)pyridin-2-yl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To [5-(2-amino(4-pyridyloxy))-1-methylbenzimidazol-2-yl](4-chlorophenyl)amine (1 eq) in tetrahydrofuran added EDC (2 eq) and HOAT (1 eq) and N,N-disopropylethylamine (4 eq) and benzoic acid (1 eq) and the resulting mixture was stirred at ambient temperature for 16 h. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was then dried with sodium sulfate and concentrated and purified by preparative chromatography to to give N-[4-({2-[(4-chlorophenyl)amino]-1-methyl-1H-benzimidazol-5-yl}oxy)pyridin-2-yl]benzamide. MS: MH+=470.9.

Aufarbeitung

  1. customThe reaction mixture was then partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was then dried with sodium sulfate
  3. concentrationconcentrated
  4. custompurified by preparative chromatography

Quellen und Nachweise

ORD-Eintrag
ord-120da8337cd34f76ba49fc82ec421d5c
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423150B2

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