Nitrogen → (3-[2-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-1H-pyrazol-1-yl)acetonitrile

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Reaktionsgleichung

Br[C:2]1[CH:6]=[CH:5][N:4]([CH2:7][C:8]#[N:9])[N:3]=1.[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[C:21]([N:23]3[CH:32]([CH3:33])[CH2:31][C:30]4[C:25](=[CH:26][C:27](B5OC(C)(C)C(C)(C)O5)=[CH:28][CH:29]=4)[CH2:24]3)[N:20]=[C:19]([NH2:43])[N:18]=2)[CH2:13][CH2:12]1.C(=O)([O-])[O-].[Na+].[Na+].N#N>O1CCOCC1.O.Cl[Pd](Cl)(P(C(C)(C)C)(C(C)(C)C)C1C=CC(N(C)C)=CC=1)P(C1C=CC(N(C)C)=CC=1)(C(C)(C)C)C(C)(C)C>[NH2:43][C:19]1[N:20]=[C:21]([N:23]2[CH:32]([CH3:33])[CH2:31][C:30]3[C:25](=[CH:26][C:27]([C:2]4[CH:6]=[CH:5][N:4]([CH2:7][C:8]#[N:9])[N:3]=4)=[CH:28][CH:29]=3)[CH2:24]2)[CH:22]=[C:17]([N:14]2[CH2:15][CH2:16][N:11]([CH3:10])[CH2:12][CH2:13]2)[N:18]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A mixture of (3-bromo-1H-pyrazol-1-yl)acetonitrile (14.4 mg, 0.0775 mmol), 4-(4-methylpiperazin-1-yl)-6-[3-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl]pyrimidin-2-amine (18.0 mg, 0.0388 mmol), dichloro(bis{di-tert-butyl[4-(dimethylamino)phenyl]phosphoranyl})palladium (1.0 mg, 0.0014 mmol), and sodium carbonate (8.22 mg, 0.0775 mmol) in 1,4-dioxane (0.5 mL) and water (0.1 mL) was vacuumed and refilled with N2 for 3 times and then stirred at 90° C. overnight. The mixture was purified by RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+: m/z=444.2.

Aufarbeitung

customThe mixture was purified by RP-HPLC (pH=10)

Quellen und Nachweise

ORD-Eintrag: ord-aaaa5ea15c094841b19ffe52a0382009
Quelldatensatz: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08436008B2

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