Diisopropylethylamine → {(S)-1-[6-Fluoro-1-(5-fluoropyridin-3-yl)-1H-benzoimidazol-2-yl]propyl}-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine

HRID 243180Notes

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:15]=[N:16][CH:17]=[C:18]([F:20])[CH:19]=3)[C:6]=2[CH:21]=1.Cl[C:23]1[N:31]=[CH:30][N:29]=[C:28]2[C:24]=1[N:25]=[CH:26][N:27]2[CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][O:33]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:23]3[N:31]=[CH:30][N:29]=[C:28]4[C:24]=3[N:25]=[CH:26][N:27]4[CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][O:33]3)[CH2:11][CH3:12])[N:7]([C:14]3[CH:15]=[N:16][CH:17]=[C:18]([F:20])[CH:19]=3)[C:6]=2[CH:21]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (S)-1-[6-fluoro-1-(5-fluoropyridin-3-yl)-1H-benzoimidazol-2-yl]propylamine (70 mg, 0.24 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (57 mg, 0.24 mmol) and DIPEA (84 μL, 0.48 mmol) in IPA (3 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 0-7% MeOH in DCM) to afford the title compound as a pale brown oil (96 mg, 82%). LCMS (Method J): RT=3.03 min, [M+H]+=491.

Workup

temperatureAfter cooling to RT
customthe volatiles were removed in vacuo
customthe resulting residue purified by column chromatography (Si—PPC, gradient 0-7% MeOH in DCM)

Sources & evidence

ORD record: ord-ea9d620ce6ae418aab278f51885786a8
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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