Hydrochloric Acid → 3-(2,3-dihydro-1H-indol-5-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 587451Notes

Reaction equation

[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[C:4]1=[O:28])[CH3:2].Cl>CCOC(C)=O>[NH:17]1[C:18]2[C:14](=[CH:13][C:12]([N:5]3[C:6]4=[N:7][CH:8]=[CH:9][CH:10]=[C:11]4[N:3]([CH2:1][CH3:2])[C:4]3=[O:28])=[CH:20][CH:19]=2)[CH2:15][CH2:16]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of tert-butyl 5-(1-ethyl-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate (100 mg) in EtOAc (2 mL) was added 4N HCl in AcOEt solution (2.0 mL). The mixture was stirred at 50° C. for 2 h and evaporated. The residue was treated with sat.NaHCO3aq. and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo to give 3-(2,3-dihydro-1H-indol-5-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one. This residue was used for the next reaction.

Workup

customevaporated
additionThe residue was treated with sat.NaHCO3aq
extractionand extracted with AcOEt
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f6889a247d73488c9f49d3b72c9caf39
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226921B2

Reaction notes

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