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

HRID 82531

Reaction equation

HRID 82531 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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58577726HCID 58577726, compound

Product 1

HCID 585772823-(2,3-dihydro-1H-indol-5-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

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

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

Sources & evidence

ORD record
ord-0d519ca849db4459b90bd162d75d0b89
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Linked notes

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