Methanol → HCID 66868178, compound

HRID 1920663Notes

Reaction equation

HRID 1920663 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[N:15]([CH2:16][CH2:17][Cl:18])[CH:14]=[N:13][C:8]=2[C:9]([NH2:12])=[N:10][CH:11]=1)=[O:5])C.[OH-].[Na+].C1COCC1.CO>C1(C)C=CC=CC=1>[NH2:12][C:9]1[C:8]2[N:13]=[CH:14][N:15]([CH2:16][CH2:17][Cl:18])[C:7]=2[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58166288HCID 58166288, compound

Product 1

HCID 66868178HCID 66868178, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 50 mg (0.19 mmol) of 4-amino-1-[2-chloro-ethyl]-1H-imidazo[4,5-c]pyridine-7-carboxylic acid ethyl ester (example 10 step B) and 1.1 ml of a 2M aqueous solution of NaOH were added 0.3 ml of THF and 0.8 ml of MeOH. The mixture was stirred for 2.5 hours at room temperature. MeOH and THF were evaporated under reduced pressure and the pH of the remaining mixture was adjusted to pH=2 with 2N aqueous HCl. The product precipitated and was isolated by filtration. Toluene was added to the product and the solvent was evaporated. This process was repeated three times. Finally 24 mg (53%) of the desired product were isolated as a light grey solid.

Workup

  1. customMeOH and THF were evaporated under reduced pressure
  2. customThe product precipitated
  3. customwas isolated by filtration
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-faca89e994d04e859fbd6e1b721ce5f0
Source dataset
uspto-grants-2012_05
Patent number
US08173609B2

Reaction notes

Loading…