Water → 4-{4-[4-(3-Sulfamoyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester

HRID 1947046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947046
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH2:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].CCN(C(C)C)C(C)C.C(S([C:28]1[N:33]=[C:32]([N:34]2[C:42]3[C:37](=[C:38]([O:43][CH2:44][CH2:45][CH2:46][S:47]([NH2:50])(=[O:49])=[O:48])[CH:39]=[CH:40][CH:41]=3)[CH:36]=[CH:35]2)[CH:31]=[CH:30][N:29]=1)=O)CCC.O>CN1C(=O)CCC1>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:28]2[N:33]=[C:32]([N:34]3[C:42]4[C:37](=[C:38]([O:43][CH2:44][CH2:45][CH2:46][S:47](=[O:48])(=[O:49])[NH2:50])[CH:39]=[CH:40][CH:41]=4)[CH:36]=[CH:35]3)[CH:31]=[CH:30][N:29]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 409963Ethyl 4-aminocyclohexanecarboxylateHCID 69308577HCID 69308577, Verbindung

Produkt 1

HCID 597434464-{4-[4-(3-Sulfamoyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

4-Aminocyclohexane carboxylic acid ethyl ester (588.4 mg, 3.44 mmol) was dissolved in NMP (5 mL) and treated with DIEA (0.993 mL, 5.7 mmol) and the reaction mixture allowed to stir at RT for 5 min. 3-[1-(2-Butylsulfinyl-pyrimidin-4-yl)-1H-indol-4-yloxy]-propane-1-sulfonic acid amide (500 mg, 1.14 mmol) was then added, and the reaction mixture heated to 120° C. for 1 h. The reaction was then allowed to cool to RT, water was added, the mixture was sonicated, filtered, and the solid dried in vacuo to yield 4-{4-[4-(3-sulfamoyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester (Compound 318).

Aufarbeitung

  1. temperaturethe reaction mixture heated to 120° C. for 1 h
  2. temperatureto cool to RT
  3. customthe mixture was sonicated
  4. filtrationfiltered
  5. customthe solid dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-49653b28e6584befa0a49993d4e475b8
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399462B2

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