Water → HCID 178462970, compound

HRID 1429942Notes

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]([CH2:19][CH3:20])[C:11]3=[O:21])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:23]1[NH:31][C:26]2=[N:27][CH:28]=[CH:29][CH:30]=[C:25]2[N:24]=1.O>CN1C(=O)CCC1>[CH2:19]([N:12]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[N:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[N:1]([C:23]2[NH:31][C:26]4=[N:27][CH:28]=[CH:29][CH:30]=[C:25]4[N:24]=2)[CH2:2][CH2:3]3)[C:11]1=[O:21])[CH3:20]

Participants

Conditions

Temperature: 150 °C

Procedure

Under nitrogen atmosphere, a mixture of 3-(2,3-dihydro-1H-indol-5-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (100 mg) and 2-chloro-3H-imidazo[4,5-b]pyridine (60.3 mg) in NMP (4 mL) was stirred at 150° C. for 2 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by prep. HPLC. Crystallization from EtOH/H2O to give the title compound (18.0 mg).

Workup

extractionextracted with AcOEt
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by prep
customCrystallization from EtOH/H2O

Sources & evidence

ORD record: ord-a974f5c03ec744d5b3f059b02b1d46a2
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940758B2

Reaction notes

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