N-methylthiophen-3-amine → HCID 68108327, Verbindung

HRID 1809737

Reaktionsgleichung

Reaktionsgleichung von HRID 1809737
Br[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][C:13]([NH:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[N:14][CH:15]=3)[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[S:34]1[CH:38]=[CH:37][C:36](NC)=[CH:35]1.[CH3:41][N:42](C1C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=CC=CC=1)C.C(O[Na])(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[N:20]1([CH2:19][CH2:18][NH:17][C:13]2[N:12]=[C:11]3[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:9]=[C:8]([C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([NH:42][CH2:41][C:36]5[CH:37]=[CH:38][S:34][CH:35]=5)[N:7]=4)[C:16]3=[CH:15][N:14]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Komponenten

7

Edukt 4

HCID 642344N-methylthiophen-3-amineHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 86667960[3-(6-bromo-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amineHCID 178418730sodium 2-methylpropan-2-olate

Produkt 1

HCID 68108327HCID 68108327, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A sealed tube was charged with [3-(6-bromo-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine (from Example 32 supra) (320 mg, 0.60 mmol), thiophen-3-yl-methylamine (81 mg, 0.72 mmol), Pd2(dba)3 (34 mg), DavePhos (47 mg), t-BuONa (69 mg, 0.72 mmol) and dioxane (12 mL). The mixture was stirred at 105° C. under an atmosphere of N2 for 8 hours. After cooling to room temperature, the mixture was filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 16 g, 100-200 mesh, eluting with MeOH:dichloromethane, 1:100 to 1:80) to give crude (2-morpholin-4-yl-ethyl)-[3-{6-[(thiophen-3-ylmethyl)-amino]-pyridin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-amine as a yellow oil. (Yield 149 mg).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel, 16 g, 100-200 mesh, eluting with MeOH:dichloromethane, 1:100 to 1:80)

Quellen und Nachweise

ORD-Eintrag
ord-4a051e2fb0b14a8393547a84528e151e
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362023B2

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