Methanesulfonic Acid → 2-(6-chloro-1H-benzo[d]imidazol-1-yl)-8-methyl-6-(pyridin-4-yl)-9-(tetrahydro-2H-pyran-4-yl)-9H-purine

HRID 600418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600418
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:17]=[C:16]3[C:12]([N:13]=[C:14]([CH3:24])[N:15]3[CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:11]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[N:10]=2)[C:5]([NH2:31])=[CH:4][CH:3]=1.[CH3:32]OC(OC)OC.CS(O)(=O)=O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:31]=[CH:32][N:8]([C:9]3[N:17]=[C:16]4[C:12]([N:13]=[C:14]([CH3:24])[N:15]4[CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[C:11]([C:25]4[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=4)[N:10]=3)[C:6]=2[CH:7]=1

Komponenten

5

Edukt 3

HCID 6395Methanesulfonic AcidHCID 9005Trimethyl orthoformateHCID 670596105-chloro-N1-(8-methyl-6-(pyridin-4-yl)-9-(tetrahydro-2H-pyran-4-yl)-9H-purin-2-yl)benzene-1,2-diamine

Produkt 1

HCID 461746802-(6-chloro-1H-benzo[d]imidazol-1-yl)-8-methyl-6-(pyridin-4-yl)-9-(tetrahydro-2H-pyran-4-yl)-9H-purineAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a vial containing crude 5-chloro-N1-(8-methyl-6-(pyridin-4-yl)-9-(tetrahydro-2H-pyran-4-yl)-9H-purin-2-yl)benzene-1,2-diamine (0.035 mmol) was added anhydrous methanol (2.5 mL), followed by anhydrous trimethylorthoformate (0.5 mL) and methane sulfonic acid (catalytic amount) and the reaction mixture was stirred under Ar at room temperature for 4 h (HPLC monitoring). Preparative HPLC purification, after evaporation of solvent and drying, provided the desired product (3.5 mg, 22% yield on two steps), as a yellow oil. TFA salt. 1H NMR (300 MHz, CD3OD+CDCl3) δ, ppm: 9.32 (s, 1H), 8.91 (br m, 4H), 8.79 (s, 1H), 7.78 (d, J=8.6 Hz, 1H), 7.43 (d, J=8.6 Hz, 1H), 4.76-4.72 (m, 1H), 4.32-4.29 (m, 2H), 3.72 (app t, J=11.7 Hz, 2H), 3.08-3.05 (m, 2H), 2.87 (s, 3H), 2.02 (br d, J=10.9 Hz, 2H); MS (EI) m/z 446.3 (MH)+.

Aufarbeitung

  1. customPreparative HPLC purification
  2. customafter evaporation of solvent
  3. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-b6dcc75e83bd459cbad99996946e3e6c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902187B2

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