Hydrochloric Acid → HCID 178432415, compound

HRID 1588581Notes

Reaction equation

HRID 1588581 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[N:10][C:5]2=[CH:4][C:3]=1[NH:11]C(=O)CCCC.Cl.C([O-])(O)=O.[Na+]>CO.CCOC(C)=O>[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[N:10][C:5]2=[CH:4][C:3]=1[NH2:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178447202HCID 178447202, compound

Product 1

HCID 178432415HCID 178432415, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-butyl-3-[2'-(1,1-dimethylethyl)aminosulfonyl][1,1'-biphenyl]-4-yl]methyl]-5-methyl-6-[(1-oxopentyl)amino]-3H-imidazo[4,5-b]pyridine (347 mg, 0.589 mmol) in MeOH (3 mL) was added conc. HCl (2 mL). After the solution was stirred at rt for 42 h, the solution was diluted with EtOAc, neutralized by saturated aq. NaHCO3, washed with brine, and dried over anhydrous MgSO4. Concentration followed by flash chromatography (100% EtOAc, 10% MeOH/EtOAc) afforded 2-butyl-3-[2'-(1,1-dimethylethyl)aminosulfonyl][1,1'-biphenyl]4-yl]methyl]-5-methyl-6-amino-3H-imidazo[4,5-b] pyridine as a solid. To this solid (100 mg, 0.198 mmol) and DMAP (10 mg, 0.08 mmol) in pyridine (2 mL) was added iso-propylisocyanate (24 mL, 0.24 mmol). After the solution was stirred at rt for 18 h, the solution was quenched with MeOH, and stirred at rt for additional 2 h. Concentration gave a brown glass, which was dissolved in TFA (2 mL) and stirred at rt for 18 h. After TFA was removed in vacuo, the residue was dissolved in EtOAc and washed with saturated aq. NaHCO3. The aqueous layer was extracted with EtOAc (2X). The combined organic layer was washed with brine, and dried over anhydrous MgSO4. Concentration followed by flash chromatography (hexanes: EtOAc=1:1, 100% EtOAc, 10% MeOH/EtOAc) afforded the title compound as a foamy powder.

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationConcentration

Sources & evidence

ORD record
ord-e26a2df035a542a190c05f6c77d2a6c9
Source dataset
uspto-grants-1993_06
Patent number
US05223499

Reaction notes

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