Sodium Hydroxide → HCID 68288265, compound

HRID 541193Notes

Reaction equation

HRID 541193 reaction equation
C[O:2][C:3]([C:5]1[C:6]([CH3:28])=[CH:7][C:8]([CH3:27])=[C:9]([C:11]2[NH:26][C:14]3[CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18][C:13]=3[N:12]=2)[CH:10]=1)=[O:4].[OH-].[Na+]>CO.O>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][C:13]2[N:12]=[C:11]([C:9]3[C:8]([CH3:27])=[CH:7][C:6]([CH3:28])=[C:5]([CH:10]=3)[C:3]([OH:4])=[O:2])[NH:26][C:14]=2[CH2:15]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68288551HCID 68288551, compound2×

Product 1

HCID 68288265HCID 68288265, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of tert-butyl 2-(5-(methoxycarbonyl)-2,4-dimethylphenyl)-6,7-dihydro-3H-imidazo[4,5-c]pyridine-5(4H)-carboxylate (compound 2.6, 300 mg, 0.70 mmol, 1.00 equiv, 90%) and sodium hydroxide (62 mg, 1.55 mmol, 2.00 equiv) in 15 mL methanol/H2O (2:1) was stiffed for at 40° C. in an oil bath. After 2 h, the reaction mixture was concentrated to about ⅓ of the volume under reduced pressure. The pH value of the remaining mixture was adjusted to 3-4 with hydrogen chloride (aq., 1 M). The resulting solids were collected by filtration and dried in an oven under reduced pressure to yield 0.2 g (69%) of the title compound as a yellow solid.

Workup

  1. customwas stiffed for at 40° C. in an oil bath
  2. concentrationthe reaction mixture was concentrated to about ⅓ of the volume under reduced pressure
  3. filtrationThe resulting solids were collected by filtration
  4. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-c10142d143564e1ba81133c3cd84945d
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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