2-Aminothiazole → HCID 86653790, Verbindung

HRID 85117

Reaktionsgleichung

Reaktionsgleichung von HRID 85117
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]2[NH:24][C:23]3[CH:25]=[CH:26][CH:27]=[C:28]([C:29](O)=[O:30])[C:22]=3[N:21]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:32]1[CH:36]=[CH:35][N:34]=[C:33]1[NH2:37].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[S:32]1[CH:36]=[CH:35][N:34]=[C:33]1[NH:37][C:29]([C:28]1[C:22]2[N:21]=[C:20]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[O:13][CH:10]3[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]3)[NH:24][C:23]=2[CH:25]=[CH:26][CH:27]=1)=[O:30]

Komponenten

7

Edukt 4

HCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 672015052-(2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yloxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid

Produkt 1

HCID 86653790HCID 86653790, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yloxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid (31; 150 mg, 0.36 mmol), thiazol-2-amine (4; 35.5 mg, 0.36 mmol), and HATU (202 mg, 0.53 mmol) in DMF (5 mL) was added DIEA (137 mg, 1.06 mmol). The mixture was stirred at room temperature for 18 h. It was then diluted with water (20 mL) and stirred for 30 min. The precipitate was collected by filtration, and then purified by column chromatography to give 85 mg of the title compound 32 (yield: 48%). MS (ESI) calcd for C26H27N5O4S: 505.18; found: 506 [M+H].

Aufarbeitung

  1. stirringstirred for 30 min
  2. filtrationThe precipitate was collected by filtration
  3. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-989dc590c2ba425ea577f04c9b5db245
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846947B2

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