Diisopropylethylamine → [(R)-2-Benzyloxy-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-(7H-purin-6-yl)amine

HRID 242925

Reaktionsgleichung

[CH2:1]([O:8][CH2:9][C@H:10]([NH2:27])[C:11]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:13]=2[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:29]1[N:37]=[CH:36][N:35]=[C:34]2[C:30]=1[N:31]=[CH:32][N:33]2C1CCCCO1.CCN(C(C)C)C(C)C>C(O)CCC>[CH2:1]([O:8][CH2:9][C@H:10]([NH:27][C:29]1[N:37]=[CH:36][N:35]=[C:34]2[C:30]=1[NH:31][CH:32]=[N:33]2)[C:11]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:13]=2[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A mixture of (R)-2-benzyloxy-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine (298 mg, 0.83 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (200 mg, 0.83 mmol) and DIPEA (700 μL, 4.2 mmol) in n-butanol (5 mL) was heated at 90° C. in a sealed vial for 48 h. After cooling to RT, the volatiles were removed in vacuo and the resulting residue loaded onto an Isolute® SCX-2 cartridge then washed with MeOH followed by 2M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) to afford the title compound as a colourless oil (256 mg, 64%). LCMS (Method B): RT 3.26 min [M+H]+ 480.2.

Aufarbeitung

temperatureAfter cooling to RT
customthe volatiles were removed in vacuo
washthen washed with MeOH
additionThe product containing fractions
concentrationconcentrated in vacuo
customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag: ord-5fdbc1da9afb46c4968c794f45b70cce
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08653089B2

Verknüpfte Notizen

Wird geladen…