Diisopropylethylamine → HCID 68157070, compound

HRID 243170Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]3[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[C@@H:19]([NH2:21])[CH3:20])[CH:5]=[C:6]([F:8])[CH:7]=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]=[C:4]([N:9]2[C:13]3[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[C@@H:19]([NH:21][C:23]2[N:31]=[CH:30][N:29]=[C:28]3[C:24]=2[N:25]=[CH:26][N:27]3[CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[CH3:20])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (S)-1-[1-(3,5-difluorophenyl)-6-fluoro-1H-benzoimidazol-2-yl]ethylamine (206 mg, 0.71 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (169 mg, 0.71 mmol) and DIPEA (0.37 mL, 2.1 mmol) in IPA (1.4 mL) was heated in a sealed tube for 20 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 0-10% 2M NH3 in MeOH/DCM) to afford the title compound as a colourless glass (141 mg, 40%). LCMS (Method C): RT 3.38 min [M+H]+ 494. 1H NMR (CDCl3, 400 MHz): δ 8.29-8.28 (1H, m), 7.97-7.96 (1H, m), 7.72-7.68 (1H, m), 7.10-7.01 (3H, m), 6.97-6.91 (1H, m), 6.86-6.82 (1H, m), 6.37 (1H, bs), 5.79-5.67 (2H, m), 4.18-4.13 (1H, m), 3.80-3.73 (1H, m), 2.11-1.97 (3H, m), 1.80-1.63 (6H, m).

Workup

temperatureAfter cooling to RT
customthe volatiles were removed in vacuo
customthe resulting residue purified by column chromatography (Si—PPC, gradient 0-10% 2M NH3 in MeOH/DCM)

Sources & evidence

ORD record: ord-e83cfefa9128438f8b3d193c5c38e2f9
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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