Diisopropylethylamine → [(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)propyl]-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine

HRID 243183Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH2:13])[CH2:11][CH3:12])[N:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1.Cl[C:22]1[N:30]=[CH:29][N:28]=[C:27]2[C:23]=1[N:24]=[CH:25][N:26]2[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1.CCN(C(C)C)C(C)C>CC(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH:13][C:22]3[N:30]=[CH:29][N:28]=[C:27]4[C:23]=3[N:24]=[CH:25][N:26]4[CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[CH2:11][CH3:12])[N:7]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:6]=2[CH:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)propylamine (55 mg, 0.20 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (49 mg, 0.20 mmol) and DIPEA (105 μL, 0.60 mmol) in IPA (0.5 mL) was heated for 24 h at 90° C. After cooling to RT, the volatiles were removed in vacuo and the resulting residue purified by column chromatography (Si—PPC, gradient 0-5% MeOH in DCM) to afford the title compound as a pale brown oil (84 mg, 89%). LCMS (Method J): RT=3.30 min, [M+H]+=471.

Workup

temperatureAfter cooling to RT
customthe volatiles were removed in vacuo
customthe resulting residue purified by column chromatography (Si—PPC, gradient 0-5% MeOH in DCM)

Sources & evidence

ORD record: ord-12004e5bd87e4aa09e136b67e8f60710
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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