Methanol → HCID 69156547, compound

HRID 2303306Notes

Reaction equation

HRID 2303306 reaction equation
[ClH:1].O1CCOCC1.[NH2:8][CH2:9][CH2:10][NH:11][C:12]1[N:17]=[C:16]([NH:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([OH:24])=[O:23])[C:15]([C:28](=[O:30])[NH2:29])=[CH:14][N:13]=1.CO>O>[ClH:1].[ClH:1].[NH2:8][CH2:9][CH2:10][NH:11][C:12]1[N:17]=[C:16]([NH:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([OH:24])=[O:23])[C:15]([C:28](=[O:30])[NH2:29])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 18460852HCID 18460852, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 69156547HCID 69156547, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A 12 ml portion of 4 M hydrochloric acid-dioxane solution was added to a mixture of 580 mg of tert-butyl ester of 3-[2-(2-aminoethylamino)-5-carbamoylpyrimidin-4-ylamino]benzoic acid with 6 ml of methanol and 6 ml of water and stirred at 80° C. for 1 hour. The organic solvent was evaporated from the reaction mixture under a reduced pressure, and the thus formed precipitate was collected by filtration. After adding methanol and water, the mixture was heated. The insoluble matter was removed by filtration and then the mother liquid was concentrated under a reduced pressure. By recrystallizing the resulting residue from a mixed solvent of methanol and water, 59 mg of 3-[2-(2-aminoethylamino)-5-carbamoylpyrimidin-4-ylamino]benzoic acid dihydrochloride was obtained (colorless crystals).

Workup

  1. customThe organic solvent was evaporated from the reaction mixture under a reduced pressure
  2. filtrationthe thus formed precipitate was collected by filtration
  3. additionAfter adding methanol and water
  4. temperaturethe mixture was heated
  5. customThe insoluble matter was removed by filtration
  6. concentrationthe mother liquid was concentrated under a reduced pressure
  7. customBy recrystallizing the resulting residue from a mixed solvent of methanol and water

Sources & evidence

ORD record
ord-b1071e20a2ff46889ab23e753682d373
Source dataset
uspto-grants-2002_08
Patent number
US06432963B1

Reaction notes

Loading…