Sodium Bicarbonate → 3-[1-(3H-imidazo[4,5-b]pyridin-2-yl)-2,3-dihydro-1H-indol-5-yl]-1-(1-methylethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 1044193

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:14]4=[N:15][CH:16]=[CH:17][CH:18]=[C:13]4[N:12]([CH:19]([CH3:21])[CH3:20])[C:11]3=[O:22])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:24]1[NH:32][C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[N:25]=1.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1>[N:25]1[C:26]2[C:27](=[N:28][CH:29]=[CH:30][CH:31]=2)[NH:32][C:24]=1[N:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:14]4=[N:15][CH:16]=[CH:17][CH:18]=[C:13]4[N:12]([CH:19]([CH3:20])[CH3:21])[C:11]3=[O:22])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 3-(2,3-dihydro-1H-indol-5-yl)-1-(1-methylethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (200 mg) and 2-chloro-3H-imidazo[4,5-b]pyridine (115 mg) in NMP (4 mL) was stirred at 140° C. for 1.5 h, treated with saturated NaHCO3, and extracted with AcOEt. The organic layer was dried over MgSO4, passed through celite pad covered with activated carbon and concentrated in vacuo. The residue was purified by prep. HPLC. The product was crystallized from EtOH/hexane to give the title compound (15.0 mg).

Workup

extractionextracted with AcOEt
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by prep
customThe product was crystallized from EtOH/hexane

Sources & evidence

ORD record: ord-05a180ac49524d56801fa6329f24164e
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563575B2

Linked notes

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