4-[2-methyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]benzoic Acid → N-[4-(2-Dimethylaminoethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-6-yl]-2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxamide

HRID 1292026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1292026
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[C:11]([CH3:13])[O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=1.[NH2:23][C:24]1[CH:25]=[CH:26][C:27]2[O:32][CH2:31][C:30](=[O:33])[N:29]([CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])[C:28]=2[CH:39]=1>S(Cl)(Cl)=O>[CH3:37][N:36]([CH3:38])[CH2:35][CH2:34][N:29]1[C:28]2[CH:39]=[C:24]([NH:23][C:20]([C:17]3[CH:18]=[CH:19][C:14]([C:3]4[CH:4]=[CH:5][C:6]([C:8]5[N:12]=[C:11]([CH3:13])[O:10][N:9]=5)=[CH:7][C:2]=4[CH3:1])=[CH:15][CH:16]=3)=[O:21])[CH:25]=[CH:26][C:27]=2[O:32][CH2:31][C:30]1=[O:33]

Komponenten

4

Edukt 2

HCID 111301684-[2-methyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]benzoic AcidHCID 189140886-amino-4-[2-(dimethylamino)ethyl]-3,4-dihydro-2H-1,4-benzoxazin-3-one

Produkt 1

HCID 18914075N-[4-(2-Dimethylaminoethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-6-yl]-2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxamideAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

2'-Methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxylic acid (EP 0553268A1) (0.188 g, 0.64 mmol) was converted to the acyl chloride by stirring at reflux under Ar in thionyl chloride (10 ml) for 45 min, cooling, and then evaporating to dryness. This was reacted with 6-amino-4(2-dimethylaminoethyl)-1,4-benzoxazin-3(4H)-one (D8) (0.150 g, 0.64 mmol) following the procedure of Example 1. This gave the title compound (0.247 g, 75%) as a white foam, which was converted to the oxalate, a white solid.

Aufarbeitung

  1. temperaturecooling
  2. customevaporating to dryness

Quellen und Nachweise

ORD-Eintrag
ord-02bc4bbb3d9f4161bd866fa710d4628b
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05756496

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