N,N,N',N'-Tetramethylethylenediamine → HCID 58577314, compound

HRID 82518Notes

Reaction equation

C[Si](C)(C)CCOC[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:27]3=[N:28][CH:29]=[CH:30][CH:31]=[C:26]3[NH:25][C:24]2=[O:32])=[CH:19][CH:18]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CN(CCN(C)C)C>C1COCC1>[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[O:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[C:27]3=[N:28][CH:29]=[CH:30][CH:31]=[C:26]3[NH:25][C:24]2=[O:32])=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-{4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (300 mg), 1 M TBAF in THF (6.3 mL), and TMEDA in THF (20 ml) was heated at 50° C. for 24 h. After cooling to rt, the mixture was partitioned between AcOEt and H2O. The organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography (SiO2, hexane/AcOEt=1/3 then AcOEt/MeOH=95/5). The obtained product was recrystallized from MeOH-iPr2O to give 3-[4-(1H-benzimidazol-2-yloxy)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (75 mg) as white crystals.

Workup

temperatureAfter cooling to rt
customthe mixture was partitioned between AcOEt and H2O
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
customevaporated
customThe residue was purified by column chromatography (SiO2, hexane/AcOEt=1/3
customThe obtained product was recrystallized from MeOH-iPr2O

Sources & evidence

ORD record: ord-25c6216edda94a21a59098557868ed13
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846713B2

Reaction notes

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