Dabco → HCID 178520468, compound

HRID 1994154Notes

Reaction equation

N12CCN(CC1)CC2.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:27])/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=2)=[CH:12][C:11]=1[C:28]([F:31])([F:30])[F:29].Cl[C:33]1[N:41]=[CH:40][N:39]=[C:38]2[C:34]=1[N:35]=[CH:36][NH:37]2>ClCCCl.[Cl-].[Na+].O>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:27])/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:33]3[N:41]=[CH:40][N:39]=[C:38]4[C:34]=3[N:35]=[CH:36][NH:37]4)[CH:21]=2)=[CH:12][C:11]=1[C:28]([F:29])([F:30])[F:31]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 1,4-diazabicyclo[2.2.2]octane (0.098 g, 0.87 mmol) in DCE (25 mL) was added (2E)-N-[4-chloro-3-(trifluoromethyl)phenyl]-3-(3-hydroxyphenyl)-acrylamide (300 mg, 0.87 mmol) and 6-chloro-9H-purine (1.95 mmol). TEA (366 μL, 2.61 mmol) was added, and the resulting solution was stirred at 60° C. The solution was diluted with brine and extracted with EtOAc. The combined organic solutions were dried over Na2SO4, filtered and concentrated. Purification by column chromatography (SiO2, 10-80% EtOAc in hexanes) provided the title compound as a white solid (45 mg). 1H NMR (400 MHz, d6-DMSO): 813.68 (br s, 1H), 10.67 (s, 1H), 8.55 (bs, 1H), 8.45 (s, 1H), 8.30 (s, 1H), 7.92 (dd, 1H), 7.70 (d, 1H), 7.65 (s, 1H), 7.60 (m, 2H), 7.38 (d, 1H) and 6.80 (d, 1H). LCMS, AA: Rt=1.71 min, [MH+ 460.0].

Workup

extractionextracted with EtOAc
dry with materialThe combined organic solutions were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customPurification by column chromatography (SiO2, 10-80% EtOAc in hexanes)

Sources & evidence

ORD record: ord-623987f9cfcf41bdaf3ef6e6ad5851a8
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652041B2

Reaction notes

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