Hydrochloric Acid → 4-[4-Methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid

HRID 1066508

Reaction equation

HRID 1066508 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[C:7]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=2)(=[O:21])=[O:20])[N:6]=[C:5]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([C:35](N)=[O:36])[CH:30]=2)[N:4]=1.Cl.C1C[O:42]CC1>C1COCC1.O1CCOCC1>[CH3:1][O:2][C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[C:7]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=2)(=[O:21])=[O:20])[N:6]=[C:5]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([C:35]([OH:42])=[O:36])[CH:30]=2)[N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8028TetrahydrofuranHCID 537796624-[4-Methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid amide2×

Product 1

HCID 98929854-[4-Methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22018518Dioxane tetrahydrofuranSolvent

Procedure

1 g of 4-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid amide, product of example 20, dissolved in a mixture of THF/dioxane (40 ml/30 ml) were treated at RT with 3N HCl (40 ml) and the solution was refluxed for 24 h, further THF (12 ml) and 3M HCl (12 ml) was then added and the solution was heated to reflux for further 24 h until the transformation was complete according to TLC analysis. The reaction mixture was concentrated in vacuo and the product was extracted into CH2Cl2. The organic layer was dried over Na2SO4, the solvent removed in vacuo. The remaining crystalline solid was washed with ether and dried in a vacuum to give 4-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid as an off-white solid. ISN mass spectrum, m/e 522 (M−1 calculated for C24H21N5O7S: 522).

Workup

  1. temperaturethe solution was refluxed for 24 h
  2. temperaturethe solution was heated
  3. temperatureto reflux for further 24 h until the transformation
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. extractionthe product was extracted into CH2Cl2
  6. dry with materialThe organic layer was dried over Na2SO4
  7. customthe solvent removed in vacuo
  8. washThe remaining crystalline solid was washed with ether
  9. customdried in a vacuum

Sources & evidence

ORD record
ord-600c67ba4942435185fd967c366acc41
Source dataset
uspto-grants-2001_06
Patent number
US06242601B1

Linked notes

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