Hexafluorophosphate → 3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acid (1-methyl-piperidin-4-yl)-amide

HRID 1667699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667699
[C:1]([C:4]1[S:8][C:7]([N:9]2[C:13]3[CH:14]=[C:15]([C:18]([OH:20])=O)[CH:16]=[CH:17][C:12]=3[N:11]=[CH:10]2)=[N:6][C:5]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)(=[O:3])[NH2:2].[NH2:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.[CH3:35]N(C(N(C)C)=[N+]1C2C(=NC=CC=2)N=N1)C.F[P-](F)(F)(F)(F)F>O.CN(C)C=O>[CH3:35][N:32]1[CH2:33][CH2:34][CH:29]([NH:28][C:18]([C:15]2[CH:16]=[CH:17][C:12]3[N:11]=[CH:10][N:9]([C:7]4[S:8][C:4]([C:1](=[O:3])[NH2:2])=[C:5]([C:21]5[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=5)[N:6]=4)[C:13]=3[CH:14]=2)=[O:20])[CH2:30][CH2:31]1

Komponenten

7

Edukt 4

HCID 9886HexafluorophosphateHCID 4243614-PiperidinamineHCID 674273413-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acidHCID 178484285HCID 178484285, Verbindung

Produkt 1

HCID 468305793-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acid (1-methyl-piperidin-4-yl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 0.060 g (0.15 mmole) of 3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acid (I.10a), 0.06 mL of 4-aminopiperidine, 0.070 g (0.18 mmole) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium, 3-oxide, hexafluorophosphate(1-) (1:1) and 4 mL of dimethylformamide was stirred at room temperature for 16 hours. The mixture was poured into 50 mL of water and extracted three times with 25 mL of ethyl acetate. The combined organic extracts were washed three times with 20 mL of 1 M hydrochloric acid. The combined aqueous extracts were made basic with potassium carbonate, and the resulting solid collected by filtration, washed with water, and air-dried to give 0.038 g of 3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-yl]-3H-benzoimidazole-5-carboxylic acid (1-methyl-piperidin-4-yl)-amide (I.10) as a light yellow solid. MH+/Z=495

Aufarbeitung

  1. extractionextracted three times with 25 mL of ethyl acetate
  2. washThe combined organic extracts were washed three times with 20 mL of 1 M hydrochloric acid
  3. filtrationthe resulting solid collected by filtration
  4. washwashed with water
  5. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-685e7e24d4d64b43ac9f54549bb44efd
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

Notizen zur Reaktion

Wird geladen…