1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborate → Tert-butyl 2-(3-(6-(3-acetamidophenyl)pyrazin-2-ylamino)phenoxy)ethylcarbamate

HRID 16271

Reaktionsgleichung

Reaktionsgleichung von HRID 16271
[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].[NH2:18][C:19]1[CH:20]=[C:21]([CH:33]=[CH:34][CH:35]=1)[O:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].F[B-](F)(F)F.C(C1C=CC=C(C(C)C)C=1[N+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C=1)(C)C.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>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[N:12]=[C:13]([NH:18][C:19]3[CH:20]=[C:21]([CH:33]=[CH:34][CH:35]=3)[O:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:14]=[N:15][CH:16]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 113750061,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborateHCID 11557882tert-butyl N-[2-(3-aminophenoxy)ethyl]carbamateHCID 116874302-(3-Acetamidophenyl)-6-chloropyrazineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 11669852Tert-butyl 2-(3-(6-(3-acetamidophenyl)pyrazin-2-ylamino)phenoxy)ethylcarbamateAusbeute 43 %

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), tert-butyl 2-(3-aminophenoxy)ethylcarbamate (CJS 700, 190 mg, 0.753 mmol), tris(dibenzylideneacetone) dipalladium (0) (28 mg, 0.030 mmol), 1,3-bis(2,6-di-i-propylphenyl)-4,5-dihydro-imidazolium tetra-fluoroborate (29 mg, 0.061 mmol) and potassium tert-butoxide (102 mg, 0.91 mmol), and dioxane (3.5 mL) were reacted at 100° C. for 20 minutes with microwave heating. The reaction mixture was filtered and washed with ethyl acetate (45 mL). The resulting liquid was dried under vacuo to give a paste that was chromatographed using a mixture of ethyl acetate:dichloromethane (1:1) as eluent to furnish 120 mg of the title compound. Yield: 43%. 1H NMR (250 MHz, DMSO-d6) δ 1.37 (s, 9 H), 2.09 (s, 3 H), 3.32 (m, 2 H), 3.98 (m, 2 H), 6.56 (dd, 1 H, Ja=8.0 Hz, Jb=2.4 Hz), 7.01 (bt, 1 H), 7.25 (t, 1 H, J=8.1 Hz), 7.36 (bd, 1 H, J=8.4 Hz), 7.45 (t, 1 H, J=7.9 Hz), 7.59 (bs, 1 H), 7.66 (bd, 1 H, J=9.2 Hz), 7.74 (bd, 1 H, J=8.0 Hz), 8.19 (s, 1 H), 8.34 (bs, 1 H), 8.42 (s, 1 H), 9.60 (s, 1 H), 10.09 (s, 1 H). 13C NMR (62.5 MHz, DMSO-d6) δ 23.99, 28.18, 66.23, 77.77, 103.95, 107.82, 110.74, 117.11, 120.07, 121.24, 129.24, 129.66, 130.08, 133.66, 137.10, 139.90, 141.88, 147.96, 151.44, 155.65, 158.87, 168.53. m/z 364.2 [(M-Boc+H)+ calc for C20H21N5O2 363.2].

Aufarbeitung

  1. customwere reacted at 100° C. for 20 minutes with microwave heating
  2. filtrationThe reaction mixture was filtered
  3. washwashed with ethyl acetate (45 mL)
  4. customThe resulting liquid was dried under vacuo
  5. customto give a paste that
  6. customwas chromatographed
  7. additiona mixture of ethyl acetate:dichloromethane (1:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-b8122c443f1c4241b9928308d5373c4d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737152B2

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