Diisopropylethylamine → HCID 178456067, compound

HRID 243388Notes

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][N: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]2C1CCCCO1.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][NH:26]4)[CH2:11][CH3:12])[N:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[C:6]=2[CH:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (S)-1-(6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)propylamine (348 mg, 1.3 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (310 mg, 1.3 mmol) and DIPEA (1.1 mL, 6.4 mmol) in IPA (4 mL) was heated for 72 h at 90° C. After cooling to RT, the volatiles were removed under reduced pressure and the resulting residue loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined, concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-5% 2M NH3/MeOH in DCM) to afford 247 as a white solid (320 mg, 63%). LCMS (Method K): RT 3.17 min [M+H]+ 389.1. 1H NMR (DMSO-d6, 400 MHz): δ 12.85 (1H, br s), 8.65 (1H, s), 8.15-8.03 (2H, m), 7.99 (1H, s), 7.84-7.76 (2H, m), 7.71 (1H, dd, J=8.75, 4.90 Hz), 7.55-7.48 (1H, m), 7.20-7.08 (2H, m), 5.73 (1H, s), 2.15-2.06 (1H, m), 2.05-1.95 (1H, m), 0.90 (3H, t, J=7.30 Hz)

Workup

temperatureAfter cooling to RT
customthe volatiles were removed under reduced pressure
washThe cartridge was washed with MeOH
concentrationconcentrated in vacuo
customthe resulting residue was purified by column chromatography (Si—PCC, gradient 0-5% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record: ord-036556ae624f483ebcf2e4468b4fbc1e
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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