Triethylamine → (S)-4-Chloro-6-((1-(1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylthio)pyrimidine-5-carbonitrile

HRID 75287

Reaktionsgleichung

Reaktionsgleichung von HRID 75287
[CH3:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([C@@H:17]([NH2:19])[CH3:18])=[C:8]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH:9]=2)[CH:4]=[CH:3]1.[Cl:20][C:21]1[C:26]([C:27]#[N:28])=[C:25](Cl)[N:24]=[C:23]([S:30][CH3:31])[N:22]=1.CCN(CC)CC>C1COCC1.C(OCC)(=O)C>[Cl:20][C:21]1[C:26]([C:27]#[N:28])=[C:25]([NH:19][C@H:17]([C:7]2[N:6]=[C:5]3[CH:4]=[CH:3][N:2]([CH3:1])[C:10]3=[CH:9][C:8]=2[N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[CH3:18])[N:24]=[C:23]([S:30][CH3:31])[N:22]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 42016204,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 86707976(S)-1-(1-Methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine

Produkt 1

HCID 86707978(S)-4-Chloro-6-((1-(1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylthio)pyrimidine-5-carbonitrileAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(S)-1-(1-Methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (200 mg, 0.768 mmol) was dissolved in THF (5 mL) along with 4,6-dichloro-2-(methylthio)pyrimidine-5-carbonitrile (169 mg, 0.768 mmol) and Et3N (0.118 mL, 0.845 mmol) to give an orange suspension. The reaction mixture was stirred at room temperature for 2 h, then diluted with ethyl acetate and washed saturated aq NH4Cl (3×15 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was then loaded onto an ISCO® silica gel cartridge (12 g) and eluted using an EtOAc/Hexane gradient. The product was collected and concentrated in vacuo to afford the title compound as a white solid (200 mg, 59%). ESI-MS m/z [M+H]+ calc'd for C20H22ClN7OS, 443.95; found 444.3.

Aufarbeitung

  1. customto give an orange suspension
  2. washwashed saturated aq NH4Cl (3×15 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washeluted
  7. customThe product was collected
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6195a14d7aa54405a5fdef293843f22e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835420B2

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