Benzenamine, 4-(4-morpholinyl)- → 2-(4-Morpholinophenylamino)-6-(3-acetamidophenyl)pyrazine

HRID 16267

Reaktionsgleichung

Reaktionsgleichung von HRID 16267
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[N:15][CH:14]=[C:13](Cl)[N:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[O:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1.F[B-](F)(F)F.C(C1C=CC=C(CCC)C=1[N+]1CCN(C2C(CCC)=CC=CC=2CCC)C=1)CC.CC(C)([O-])C.[K+]>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.O1CCOCC1>[O:18]1[CH2:19][CH2:20][N:21]([C:24]2[CH:25]=[CH:26][C:27]([NH:28][C:13]3[N:12]=[C:11]([C:7]4[CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=[CH:9][CH:8]=4)[CH:16]=[N:15][CH:14]=3)=[CH:29][CH:30]=2)[CH2:22][CH2:23]1

Komponenten

7

Edukt 4

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 116874302-(3-Acetamidophenyl)-6-chloropyrazineHCID 23665647Potassium tert-butoxideHCID 866178521,3-Bis(2,6-di-1-propylphenyl)-4,5-dihydroimidazolium tetrafluoroborate

Produkt 1

HCID 115746252-(4-Morpholinophenylamino)-6-(3-acetamidophenyl)pyrazineAusbeute 29,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using Method O, 2-(3-acetamidophenyl)-6-chloropyrazine (150 mg, 0.61 mmol), 4-morpholinoaniline (155.4 mg, 0.87 mmol), tris(dibenzylideneacetone) dipalladium (0) (28 mg, 0.030 mmol), 1,3-bis(2,6-di-1-propylphenyl)-4,5-dihydro-imidazolium tetrafluoroborate (29 mg, 0.061 mmol), potassium tert-butoxide (102 mg, 0.91 mmol), and dioxane (3.5 mL) were reacted at 100° C. for 30 minutes with microwave heating. The reaction crude was passed through a short silica gel column (2 g silica), which was thoroughly washed with ethyl acetate. The last fractions of this column were collected to give 9 mg of pure title compound. The first fractions were collected, the solvent was evaporated under vacuo and the resulting solid was crystallised in ethyl acetate to produce 61 mg of the title compound. Yield: 29.8%. 1H NMR (250 MHz, DMSO-d6) δ 2.09 (s, 3 H), 3.03-3.07 (bt, 4 H), 3.72-3.76 (bt, 4 H), 6.97 (d, 2 H, J=9.0 Hz), 7.42 (t, 1 H, J=7.9 Hz), 7.65-7.68 (m, 2 H), 7.70 (d, 2H, J=8.9 Hz), 8.11 (s; 1 H), 8.33 (bs, 2 H), 9.36 (s, 1 H), 10.09 (s, 1 H); 13C NMR (62.9 MHZ, DMSO-d6) δ 24.11, 49.24, 66.16, 116.01, 117.08, 119.61, 119.89, 121.08, 129.16, 133.03, 133.15, 137.23, 139.87, 146.10, 147.95, 151.70, 168.45; m/z 390.2 [(M+H)+, calcd for C22H23N5O2 389.2].

Aufarbeitung

  1. customwere reacted at 100° C. for 30 minutes with microwave heating
  2. customThe reaction crude
  3. washwas thoroughly washed with ethyl acetate
  4. customThe last fractions of this column were collected

Quellen und Nachweise

ORD-Eintrag
ord-9d88e03a5af74bb6a37187a58cbeb9ef
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737152B2

Verknüpfte Notizen

Wird geladen…