Hydrochloric Acid → 5-(6-Amino-1-benzyl-1H-benzoimidazol-2-yl)-1,3-dimethyl-1H-pyridin-2-one

HRID 930522Notes

Reaction equation

HRID 930522 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([NH:17]C(=O)C)[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:21]1[CH:26]=[C:25]([CH3:27])[C:24](=[O:28])[N:23]([CH3:29])[CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]2[N:10]=[C:9]([C:21]3[CH:26]=[C:25]([CH3:27])[C:24](=[O:28])[N:23]([CH3:29])[CH:22]=3)[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:12]=2[CH:13]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 117891922N-[3-Benzyl-2-(1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3H-benzoimidazol-5-yl]-acetamide

Product 1

HCID 1178753515-(6-Amino-1-benzyl-1H-benzoimidazol-2-yl)-1,3-dimethyl-1H-pyridin-2-one

Conditions

Temperature
100 °C

Procedure

N-[3-Benzyl-2-(1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3H-benzoimidazol-5-yl]-acetamide I-9″ (3.000 g; 7.763 mmol) is suspended in 8 N HCl (74 mmol). The reaction mixture is stirred for 3 h at 100° C. The reaction is cooled to RT and then quenched slowly with sodium bicarbonate (until reaching a basic pH). The reaction is extracted with MeOH/DCM. The combined organic layer is dried over Na2SO4 and concentrated in vacuum.

Workup

  1. temperatureThe reaction is cooled to RT
  2. customquenched slowly with sodium bicarbonate (
  3. extractionThe reaction is extracted with MeOH/DCM
  4. dry with materialThe combined organic layer is dried over Na2SO4
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-4ba585d3cafe4695bbc01506fb14dcfb
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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