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

HRID 242922

Reaktionsgleichung

[CH2:1]([O:8][C@H:9]([CH3:28])[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:30]1[N:38]=[CH:37][N:36]=[C:35]2[C:31]=1[N:32]=[CH:33][N:34]2C1CCCCO1.CCN(C(C)C)C(C)C>C(O)CCC>[CH2:1]([O:8][C@H:9]([CH3:28])[C@H:10]([NH:27][C:30]1[N:38]=[CH:37][N:36]=[C:35]2[C:31]=1[NH:32][CH:33]=[N:34]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 (1R,2R)-2-benzyloxy-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)propylamine (100 mg, 0.27 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (65 mg, 0.27 mmol) and DIPEA (240 μL, 1.35 mmol) in n-butanol (1 mL) was heated at 90° C. in a sealed vial for 18 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 (128 mg, 96%). LCMS (Method J): RT 3.19 min [M+H]+ 494.1.

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-0327a4b9ab874b37bde8b7d27313d316
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08653089B2

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