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

HRID 1429907Notes

Reaction equation

HRID 1429907 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 58577726tert-butyl 5-(1-ethyl-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate

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-3994db18ee13458db83c610c7a49b28f
Source dataset
uspto-grants-2015_01
Patent number
US08940758B2

Reaction notes

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