2,4,6-Trimethylpyridine → N-[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexyl]-2-phenylamino-acetamide

HRID 352250

Reaktionsgleichung

Reaktionsgleichung von HRID 352250
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([N:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:18])[C:12]=3[C:11]3=[N:19][O:20][C:21]([CH3:22])=[C:10]3[C:9]2=[O:23])[CH2:3]1.[C:24]1([NH:30][CH2:31][C:32](O)=[O:33])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.ON1C2N=CC=CC=2N=N1.Cl.C(N=C=N)C.CC1C=C(C)C=C(C)N=1>CN(C)C=O>[Cl:18][C:13]1[C:12]2[C:11]3[C:10](=[C:21]([CH3:22])[O:20][N:19]=3)[C:9](=[O:23])[N:8]([CH:4]3[CH2:5][CH2:6][CH2:7][CH:2]([NH:1][C:32](=[O:33])[CH2:31][NH:30][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:3]3)[C:17]=2[CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 5

HCID 79532,4,6-TrimethylpyridineHCID 66025N-PhenylglycineHCID 181649HOAtHCID 21883477Ethylcarbodiimide hydrochlorideHCID 227137145-(3-Amino-cyclohexyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one

Produkt 1

HCID 22713799N-[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexyl]-2-phenylamino-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Anhydrous dimethylformamide (10 mL) in a nitrogen atmosphere was used to dissolve 5-(3-aminocyclohexyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin4-one (50 mg; 0.151 mmol), N-phenylglycine (29.6 mg; 0.196 mmol; 1.3 equiv), 1-hydroxy-7-azabenzotriazole (26.7 mg; 0.196 mmol; 1.3 equiv), 1-[3-(dimethylamino)propyl[-3-ethylcarbodiimide hydrochloride (37.6 mg; 0.196 mmol; 1.3 equiv), and 2,4,6-trimethylpyridine (199 μL; 1.51 mmol; 10 equiv). After overnight stirring at room temperature, the reaction solution was treated in a manner similar to Example 159. The resulting material was purified by three consecutive radial chromatography runs on a 2 mm thick silica gel rotor with a 1% methanol/dichloromethane (v/v) mobile phase, a 1% methanol/0.25% triethylamine/dichloromethane (v/v/v) mobile phase, and a 5% acetonitrile/dichloromethane mobile phase. The desired product was isolated as a white solid 56% yield (30 mg). MS(ES) calc'd: [M+M]+=465.16 m/z; [M−H]−=463.16 m/z; [M+OAc]−=523.16 m/z. Found: 465.1 m/z; 463.2 m/z; 523.2 m/z.

Aufarbeitung

  1. additionthe reaction solution was treated in a manner similar to Example 159
  2. customThe resulting material was purified by three consecutive radial chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fcc8b4782c774f81b54c7be0b35807b0
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743794B2

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