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

HRID 587488Notes

Reaction equation

HRID 587488 reaction equation
[CH3:1][CH:2]([N:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)[C:5]1=[O:29])[CH3:3].Cl>CCOC(C)=O.C1COCC1.CCOC(C)=O>[NH:18]1[C:19]2[C:15](=[CH:14][C:13]([N:6]3[C:7]4=[N:8][CH:9]=[CH:10][CH:11]=[C:12]4[N:4]([CH:2]([CH3:1])[CH3:3])[C:5]3=[O:29])=[CH:21][CH:20]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58577369tert-Butyl 5-[1-(1-methylethyl)-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl]-2,3-dihydro-1H-indole-1-carboxylate

Product 1

HCID 585772553-(2,3-dihydro-1H-indol-5-yl)-1-(1-methylethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of tert-butyl 5-[1-(1-methylethyl)-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl]-2,3-dihydro-1H-indole-1-carboxylate in AcOEt/EtOH (1/1, 10 mL) was added 4N HCl in AcOEt (4 mL). The mixture was stirred at 80° C. for 2 h, evaporated, treated with saturated NaHCO3, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was suspended in IPE and the suspension was collected by filtration to give the title compound as white crystals (313 mg).

Workup

  1. customevaporated
  2. additiontreated with saturated NaHCO3
  3. extractionextracted with AcOEt
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. filtrationthe suspension was collected by filtration

Sources & evidence

ORD record
ord-30c2d35400bf46b6bc801bdd737e9dc1
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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