Water → N-(4-fluorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 23632
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20]O)=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.N1C(C)=CC(C)=CC=1C.CS([Cl:39])(=O)=O.O>CN(C=O)C.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20][Cl:39])=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 22574394N-(4-fluorobenzyl)-2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Produkt 1

HCID 22574387N-(4-fluorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a slurry of 3.3 g (9.2 mmol) N-(4-fluorobenzyl)-2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide in 200 mL anhydrous DMF at 0° C., was added 3.0 mL (22.7 mmol) 2,4,6-collidine and 0.75 g (6.14 mmol) 4-(dimethylamino) pyridine. To this mixture, 1.8 mL (23.3 mmol) of methanesulfonyl chloride was added in two portions of 0.9 mL. The mixture was allowed to slowly warm to room temperature with stirring over night. After 19 hours, the homogeneous dark brown mixture was poured into 1.0 L of water. The resulting slurry was stirred for 2 hours at room temperature. The solids were then collected by vacuum filtration, washed with additional water, and dried in a vacuum oven at 60° C. over a weekend. This provided 2.91 g of the title compound as a tan solid.

Aufarbeitung

  1. stirringThe resulting slurry was stirred for 2 hours at room temperature
  2. filtrationThe solids were then collected by vacuum filtration
  3. washwashed with additional water
  4. customdried in a vacuum oven at 60° C. over a weekend

Quellen und Nachweise

ORD-Eintrag
ord-1b39c394c3a647ed955f74042ab4fd9e
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852731B2

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