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Diisopropylethylamine → 7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-N-(1-(1-methyl-1H-pyrazol-4-yl)ethyl)-3-nitroquinolin-4-amine

HRID 81991
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 81991
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[CH3:24][N:25]1[CH:29]=[C:28]([CH:30]([NH2:32])[CH3:31])[CH:27]=[N:26]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O>[CH3:20][C:15]1[C:14]([C:8]2[CH:7]=[C:6]3[C:11]([C:2]([NH:32][CH:30]([C:28]4[CH:27]=[N:26][N:25]([CH3:24])[CH:29]=4)[CH3:31])=[C:3]([N+:21]([O-:23])=[O:22])[CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12][CH3:13])=[C:18]([CH3:19])[O:17][N:16]=1
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Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 230057821-(1-methyl-1H-pyrazol-4-yl)ethan-1-amineHCID 574655804-(4-Chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazole2×

Produkt 1

HCID 709800257-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-N-(1-(1-methyl-1H-pyrazol-4-yl)ethyl)-3-nitroquinolin-4-amineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

4-(4-Chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazole (200 mg, 0.599 mmol, for preparation see Intermediate 8) and [1-(1-methyl-1H-pyrazol-4-yl)ethyl]amine (113 mg, 0.9 mmol) were heated in a mixture of DIPEA (0.324 ml, 1.858 mmol) and NMP (15 ml) at 120° C. for 4 h. The reaction mixture was cooled to room temperature, diluted with water (300 ml) and extracted with EtOAc (2×200 ml). The combined organic phase was washed with water (300 ml) and brine (200 ml), dried with sodium sulphate and evaporated. The resulting gum was dissolved in DCM (3 ml) loaded onto a 100 g silica cartridge and eluted with 2M methanolic ammonia/DCM (0-12%). The product-containing fractions were evaporated in vacuo to give 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(1-(1-methyl-1H-pyrazol-4-yl)ethyl)-3-nitroquinolin-4-amine (0.21 g, 0.497 mmol, 83% yield) which was used in the subsequent step without further purification. LCMS (formate) Rt 0.87 min, MH+ 423.

Aufarbeitung

  1. extractionextracted with EtOAc (2×200 ml)
  2. washThe combined organic phase was washed with water (300 ml) and brine (200 ml)
  3. dry with materialdried with sodium sulphate
  4. customevaporated
  5. dissolutionThe resulting gum was dissolved in DCM (3 ml)
  6. washeluted with 2M methanolic ammonia/DCM (0-12%)
  7. customThe product-containing fractions were evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1983b6fd8c534a8ab0918089d9c64591
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846709B2

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