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

HRID 1044154Notes

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-85c6b429175149d1b9079ede73b377b5
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563575B2

Reaction notes

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