1H-1,2,4-Triazole → (S)-2-(2-(3-(1H-1,2,4-triazol-1-yl)phenyl)-1H-imidazol-1-yl)-6a-ethyl-5-methyl-6a,7,8,9-tetrahydropyrrolo[2,1-h]pteridin-6(5H)-one

HRID 44887

Reaktionsgleichung

Reaktionsgleichung von HRID 44887
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:9]([C:13]3[N:22]=[CH:21][C:20]4[N:19]([CH3:23])[C:18](=[O:24])[C@:17]5([CH2:28][CH3:29])[CH2:25][CH2:26][CH2:27][N:16]5[C:15]=4[N:14]=3)[CH:10]=[CH:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1.[NH:30]1[CH:34]=[N:33][CH:32]=[N:31]1.CNC1CCCCC1NC.C([O-])([O-])=O.[Cs+].[Cs+]>CC(N(C)C)=O.C(Cl)Cl.[Cu](I)I>[N:30]1([C:2]2[CH:3]=[C:4]([C:8]3[N:9]([C:13]4[N:22]=[CH:21][C:20]5[N:19]([CH3:23])[C:18](=[O:24])[C@:17]6([CH2:28][CH3:29])[CH2:25][CH2:26][CH2:27][N:16]6[C:15]=5[N:14]=4)[CH:10]=[CH:11][N:12]=3)[CH:5]=[CH:6][CH:7]=2)[CH:34]=[N:33][CH:32]=[N:31]1

Komponenten

8

Edukt 4

HCID 92571H-1,2,4-TriazoleHCID 10796Cesium carbonateHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 58405315(S)-2-(2-(3-bromophenyl)-1H-imidazol-1-yl)-6a-ethyl-5-methyl-6a,7,8,9-tetrahydropyrrolo[2,1-h]pteridin-6(5H)-one

Produkt 1

HCID 58405411(S)-2-(2-(3-(1H-1,2,4-triazol-1-yl)phenyl)-1H-imidazol-1-yl)-6a-ethyl-5-methyl-6a,7,8,9-tetrahydropyrrolo[2,1-h]pteridin-6(5H)-oneAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

(S)-2-(2-(3-bromophenyl)-1H-imidazol-1-yl)-6a-ethyl-5-methyl-6a,7,8,9-tetrahydropyrrolo[2,1-h]pteridin-6(5H)-one (Example 252, 0.118 mmol, 0.050 g) was added to a solution of 1,2,4-triazole (0.593 mmol, 0.041 g), copper iodide (0.007 mmol, 0.001 g), N1,N2-dimethylcyclohexane-1,2-diamine (0.023 mmol, 0.003 g), and Cs2CO3 (0.593 mmol, 0.193 g) in 1 mL of DMA. The reaction mixture was microwaved at 185° C. for 1 h. The reaction mixture was diluted with 15 mL of DCM, washed with 5 mL of water, dried with Na2SO4, filtered and concentrated. The resulting residue was purified by reverse phase HPLC to give the title compound as a white solid (0.012 g, 23%); 1H NMR (400 MHz, CDCl3) δ: 8.83 (s, 1H), 8.12 (m, 2H), 7.95 (s, 1H), 7.90 (m, 1H), 7.69 (s, 1H), 7.60 (m, 3H), 3.37 (m, 4H), 3.20 (m, 1H), 2.35 (m, 1H), 2.26 (m, 3H), 2.00 (m, 2H), 1.77 (m, 1H), 1.62 (m, 1H), 0.78 (t, J=7.4 Hz, 3H); LCMS: 442.3 m/z (M+H)+; ret. Time: 4.722 min (Analytical Method C).

Aufarbeitung

  1. customThe reaction mixture was microwaved at 185° C. for 1 h
  2. washwashed with 5 mL of water
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cf0a866db12845c79967db5ebae7acb5
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541418B2

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