Diisopropylethylamine → HCID 178474465, compound

HRID 243394Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of (S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride (0.22 g, 0.68 mmol), N-(6-chloro-9H-purin-2-yl)acetamide (0.20 g, 0.95 mmol) and DIPEA (0.60 mL, 3.38 mmol) in IPA (2 mL) was stirred at 85° C. in a sealed tube for 16 h. The resulting mixture was diluted with DCM/methanol then concentrated in vacuo onto silica gel and this residue was purified by chromatography (SiO2, 0-15% (2M ammonia in methanol) in DCM), and then by preparative HPLC (Phenomenex Gemini 5 μm C18 on a 60 min gradient 20-98% 0.1% HCO2H in acetonitrile/water) to give 262 as a white solid (0.067 g, 23%). LCMS (method K): Rt 3.14 min, [M+H]+ 431. 1H NMR (DMSO-d6): δ 13.20-12.50 (1H, bs), 9.60 (1H, s), 8.00 (1H, s), 7.71 (1H, m), 7.60 (2H, s), 7.51-7.49 (3H, m), 7.11-7.08 (1H, m), 6.86 (1H, m), 5.64 (1H, m), 2.10 (3H, s), 1.50 (3H, d, J=6.81 Hz)

Workup

concentrationthen concentrated in vacuo onto silica gel
customthis residue was purified by chromatography (SiO2, 0-15% (2M ammonia in methanol) in DCM)

Sources & evidence

ORD record: ord-091bf79bf17b44578465da1aedab48e2
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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