5-Cyclopropyl-1,3,4-thiadiazol-2-amine → 5-Chloro-N-{2-[4-(5-cyclopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-2-methoxy-benzamide

HRID 2266403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2266403
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1)=[O:8].[CH:25]1([C:28]2[S:32][C:31]([NH2:33])=[N:30][N:29]=2)[CH2:27][CH2:26]1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](=[O:20])(=[O:19])[NH:33][C:31]2[S:32][C:28]([CH:25]3[CH2:27][CH2:26]3)=[N:29][N:30]=2)=[CH:14][CH:13]=1)=[O:8]

Komponenten

5

Edukt 2

HCID 7170215-Cyclopropyl-1,3,4-thiadiazol-2-amineHCID 44545764-(2-((5-Chloro-2-methoxyphenyl)formamido)ethyl)benzene-1-sulfonyl chloride

Produkt 1

HCID 575868185-Chloro-N-{2-[4-(5-cyclopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-2-methoxy-benzamideAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

1.1 g 4-[2-(5-Chloro-2-methoxy-benzoylamino)-ethyl]-benzenesulfonyl chloride, 483 mg 5-Cyclopropyl-[1,3,4]thiadiazol-2-ylamine and 35.0 mg 4-dimethylaminopyridine were dissolved in 5 ml pyridine and stirred under microwave irradiation at 115° C. for two hours. The pyridine was removed in vacuo and the residue coevaporated three times with portions of 20 ml toluene. The residue was purified by RP-HPLC to obtain 590 mg 5-Chloro-N-{2-[4-(5-cyclopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-2-methoxy-benzamide.

Aufarbeitung

  1. customThe pyridine was removed in vacuo
  2. customThe residue was purified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f84d6dbf280d4bed969e5300335db827
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858647B2

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