Hydrochloric Acid → HCID 86691833, compound

HRID 1616222Notes

Reaction equation

HRID 1616222 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:14]=[C:15]([CH:25]=[CH:26][CH:27]=3)[CH2:16][NH:17]C(=O)OC(C)(C)C)=[CH:10][CH:11]=2)[N:6]([CH3:28])[C:5]1=[O:29].Cl.C(OCC)(=O)C>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[NH2:17][CH2:16][C:15]1[CH:14]=[C:13]([C:9]2[N:8]=[C:7]3[N:6]([CH3:28])[C:5](=[O:29])[N:4]([CH2:3][C:2]([CH3:1])([CH3:31])[CH3:30])[C:12]3=[CH:11][CH:10]=2)[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86762488HCID 86762488, compound

Product 1

HCID 86691833HCID 86691833, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a round bottom flask, tert-butyl {3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]benzyl}carbamate (14-63) (250 mg, 0.59 mmol) was dissolved in DCM (2 mL). 4M HCl in ethyl acetate (2 ml, 8 mmol) was added and allowed to stir overnight. The reaction was diluted with sodium bicarbonate, extracted with DCM (3×), and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to produce 5-[3-(aminomethyl)phenyl]-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (23-1). MS (M+H)+: observed=325.2, calculated=325.4.

Workup

  1. extractionextracted with DCM (3×)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9666eeb398994309acb176fa7b062172
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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