2-Aminothiazole → HCID 44546587, Verbindung

HRID 85096

Reaktionsgleichung

Reaktionsgleichung von HRID 85096
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([OH:20])=O)[C:11]=2[N:10]=1.[S:23]1[CH:27]=[CH:26][N:25]=[C:24]1[NH2:28].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:23]1[CH:27]=[CH:26][N:25]=[C:24]1[NH:28][C:18]([C:17]1[C:11]2[N:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:2]([F:1])([F:22])[F:21])[NH:13][C:12]=2[CH:14]=[CH:15][CH:16]=1)=[O:20]

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 672016022-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid

Produkt 1

HCID 44546587HCID 44546587, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid (3; 75 mg, 0.24 mmol) was taken up in DMF (2 mL) along with thiazol-2-amine (4; 24 mg, 0.24 mmol) and HATU (186 mg, 0.49 mmol). DIEA (81 μL, 0.49 mmol) was added. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with water and filtered. The collected solids were further purified by silica gel chromatography to afford the desired product, namely N-(thiazol-2-yl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide (Compound 208), as a white solid (35 mg, yield: 38%). MS (ESI) calcd for C18H11F3N4OS: 388.06; found: 389 [M+H].

Aufarbeitung

  1. filtrationfiltered
  2. customThe collected solids were further purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3c2ba477f6d94fa092f40a68852f9585
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846947B2

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