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 1429945

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-60142572b13b428e9ea63f9b169517f8
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940758B2

Linked notes

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