Hexafluorophosphate → 2-(6-Benzyloxy-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide

HRID 1667732

Reaktionsgleichung

Reaktionsgleichung von HRID 1667732
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[CH:15][N:14]([C:17]3[S:18][C:19]([C:29](O)=[O:30])=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=4)[N:21]=3)[C:13]=2[CH:32]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:34](C(N(C)C)=[N+]1C2C(=NC=CC=2)N=N1)C.F[P-](F)(F)(F)(F)F.[Cl-].[NH4+].C(N(C(C)C)C(C)C)C>O.CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[CH:15][N:14]([C:17]3[S:18][C:19]([C:29]([NH2:34])=[O:30])=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=4)[N:21]=3)[C:13]=2[CH:32]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 5

HCID 9886HexafluorophosphateHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 674440732-(6-Benzyloxy-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acidHCID 178484285HCID 178484285, Verbindung

Produkt 1

HCID 674433752-(6-Benzyloxy-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amideAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 3.3 g (7.16 mmole) of 2-(6-benzyloxy-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid (I.25b), 20 mL of dimethylformamide and 3.26 g (8.59 mmole) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium, 3-oxide, hexafluorophosphate(1-) (1:1) was added 0.759 g (14.52 mmole) of ammonium chloride followed by 3.74 mL (21.48 mmole) of ethyldiisopropylamine. The mixture was stirred at ambient temperature for 1 hour and then diluted with 500 mL of water. The suspension was stirred for 30 minutes. The precipitate was collected by filtration to afford 3.2 g of 2-(6-benzyloxy-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide as an off-white solid (I.25c).

Aufarbeitung

  1. stirringThe suspension was stirred for 30 minutes
  2. filtrationThe precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-06e2d9f800ba4dea96bb3e75af0513b6
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

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