2-Dimethylaminopyridine → HCID 22119992, Verbindung

HRID 1274648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1274648
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]([CH3:26])([CH3:25])[C:22](O)=[O:23])[C:17]=3[CH:27]=2)[C:3]1=[O:28].C(Cl)(=O)C(Cl)=O.[CH3:35][S:36]([NH2:39])(=[O:38])=[O:37].C(N(C(C)C)C(C)C)C.CN(C1C=CC=CN=1)C>CN(C)C=O.C(Cl)Cl>[CH3:1][N:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]([CH3:26])([CH3:25])[C:22]([NH:39][S:36]([CH3:35])(=[O:38])=[O:37])=[O:23])[C:17]=3[CH:27]=2)[C:3]1=[O:28]

Komponenten

8

Edukt 5

HCID 218852-DimethylaminopyridineHCID 65578Oxalyl chlorideHCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 22119820HCID 22119820, Verbindung

Produkt 1

HCID 22119992HCID 22119992, VerbindungAusbeute 13,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N,N-Dimethylformamide (8 drops) is added to a mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-α,α-dimethyl-1,2-benzisothiazole-3-acetic acid (2.00 g, 0.00484 mol) and methylene chloride. The mixture is cooled on an ice bath and oxalyl chloride (2.0 M in methylene chloride, 6.05 ml, 0.0121 mol) is added. The resultant mixture is stirred one hour on an ice bath and concentrated in vacuo. The residue is taken up in tetrahydrofuran. Methylsulfonamide (0.690 g, 0.00726 mol) is added, followed by ethyldiisopropylamine (0.940 g, 0.00727 mol) and dimethylaminopyridine (0.100 g). The resultant mixture is stirred at room temperature and filtered. The filtrate is concentrated in vacuo and the residue is filtered through silica gel with hexanes:ethyl acetate. The filtrate is concentrated in vacuo to a tan solid. The solid is suspended in methylene chloride, stirred, and refiltered to give the title compound as a white solid (0.320 g, 13.5%, mp 264-265° C.).

Aufarbeitung

  1. temperatureThe mixture is cooled on an ice bath
  2. concentrationconcentrated in vacuo
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo
  5. filtrationthe residue is filtered through silica gel with hexanes
  6. concentrationThe filtrate is concentrated in vacuo to a tan solid

Quellen und Nachweise

ORD-Eintrag
ord-8fab8baf12804d5089e953babd489946
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06156700

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