1-Hydroxybenzotriazole → HCID 22012581, Verbindung

HRID 1533820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1533820
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([C:12](=[O:37])[N:13]([CH3:36])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[O:28])[CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[NH2:60][C:61]1[C:69]2[N:68]=[C:67]([CH2:70][N:71]3[CH2:76][CH2:75][N:74]([CH3:77])[CH2:73][CH2:72]3)[NH:66][C:65]=2[CH:64]=[CH:63][CH:62]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH:9]=[CH:8][C:4]=1[C:5](=[O:6])[NH:60][C:61]1[C:69]2[N:68]=[C:67]([CH2:70][N:71]3[CH2:72][CH2:73][N:74]([CH3:77])[CH2:75][CH2:76]3)[NH:66][C:65]=2[CH:64]=[CH:63][CH:62]=1)[C:12]([N:13]([CH3:36])[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]1[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]1)=[O:28])=[O:37]

Komponenten

7

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18354839HCID 18354839, VerbindungHCID 18355157HCID 18355157, Verbindung

Produkt 1

HCID 22012581HCID 22012581, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-methoxy-4-[N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-carbamoyl]benzoic acid (200 mg) in N,N-dimethylformamide (3 ml) at 0° C. were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (97 mg), N-hydroxybenzotriazole (79 mg) and 4-amino-2-[(4-methylpiperazin-1-yl)methyl]-1H-benzimidazole (105 mg) and the mixture was stirred at ambient temperature for 15 hours. The reaction mixture was poured into saturated sodium bicarbonate aqueous solution and extracted with chloroform. The organic layer was washed with saturated sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1) to give 3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-4-[2-[(4-methylpiperazin-1-yl)methyl]-1H-benzimidazol-4-yl]carbamoylbenzamide (104 mg).

Aufarbeitung

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated sodium bicarbonate aqueous solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-573095434fa34710bc79b4d223409270
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06207693B1

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