Hydrochloric Acid → 5-(4-Aminocyclohex-1-en-1-yl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 629886Notes

Reaction equation

HRID 629886 reaction equation
[CH3:1][C:2]([CH3:30])([CH3:29])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH2:18][CH2:17][CH:16]([NH:19]C(=O)OC(C)(C)C)[CH2:15][CH:14]=3)=[CH:10][CH:11]=2)[N:6]([CH3:27])[C:5]1=[O:28].C(Cl)Cl.Cl.CCOC(C)=O>CO>[NH2:19][CH:16]1[CH2:17][CH2:18][C:13]([C:9]2[N:8]=[C:7]3[N:6]([CH3:27])[C:5](=[O:28])[N:4]([CH2:3][C:2]([CH3:1])([CH3:30])[CH3:29])[C:12]3=[CH:11][CH:10]=2)=[CH:14][CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 71128770tert-Butyl {4-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]cyclohex-3-en-1-yl}carbamate

Product 1

HCID 711171075-(4-Aminocyclohex-1-en-1-yl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a round bottom flask was added tert-butyl {-4-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]cyclohex-3-en-1-yl}carbamate (17-1) (338 mg, 0.815 mmol), DCM (2 mL), MeOH (2 mL), and a 4N solution of HCl in EtOAc (2.038 ml, 8.15 mmol). The reaction mixture was then capped & stirred at room temperature for several hours. The reaction was then concentrated to yield 5-(4-Aminocyclohex-1-en-1-yl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (17-2) as a tan solid.

Workup

  1. customThe reaction mixture was then capped
  2. concentrationThe reaction was then concentrated

Sources & evidence

ORD record
ord-ae5263552e2440ad8af6dbd9897d41a2
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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