Triethylamine → HCID 178486173, Verbindung

HRID 388976

Reaktionsgleichung

Reaktionsgleichung von HRID 388976
Cl.Cl.Cl.[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]([C:16]3[C:35]([N:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)=[CH:34][C:19]4[NH:20][C:21]([NH:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[C:30]([F:33])([F:32])[F:31])=[N:22][C:18]=4[CH:17]=3)=[O:15])[CH:11]=2)[CH:6]=[N:5]1.C(N(CC)CC)C.[CH3:49][N:50]([CH3:55])[S:51](Cl)(=[O:53])=[O:52].O.NN>CN(C=O)C>[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]([C:16]3[C:35]([N:36]4[CH2:37][CH2:38][N:39]([S:51](=[O:53])(=[O:52])[N:50]([CH3:55])[CH3:49])[CH2:40][CH2:41]4)=[CH:34][C:19]4[NH:20][C:21]([NH:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[C:30]([F:31])([F:32])[F:33])=[N:22][C:18]=4[CH:17]=3)=[O:15])[CH:11]=2)[CH:6]=[N:5]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 83372Dimethylsulphamoyl chlorideHCID 178478620HCID 178478620, Verbindung

Produkt 1

HCID 178486173HCID 178486173, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 6-piperazin-1-yl-2-(2-trifluoromethylphenylamino)-1H-benzimidazole-5-carboxylic acid (1H-indazol-6-yl)-amide trihydrochloride (0.3 mmol; see Example 88) in DMF (1 mL) was added with triethylamine (1.5 mmol) and N,N-dimethylsulfamoyl chloride (0.4 mmol). The resulting mixture was stirred at RT for 4 h and added with hydrazine hydrate (2 mmol). The contents were warmed to 50° C. and stirred vigorously for 60 min. The reaction mixture was then poured into ice cold water, and the solid was filtered, washed with water, and dried under vacuum. The crude product was then purified on a silica gel column chromatography using MeOH/DCM as eluent to afford 6-(4-dimethylsulfamoyl-piperazin-1-yl)-2-(2-trifluoromethyl-phenylamino)-1H-benzoimidazole-5-carboxylic acid (1H-indazol-6-yl)-amide as a white solid. MS: m/z 628 (M+H)+.

Aufarbeitung

  1. temperatureThe contents were warmed to 50° C.
  2. stirringstirred vigorously for 60 min
  3. additionThe reaction mixture was then poured into ice cold water
  4. filtrationthe solid was filtered
  5. washwashed with water
  6. customdried under vacuum
  7. customThe crude product was then purified on a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cc0ae6472b994337b2f0860b998d65e6
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377983B2

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