Hydrochloric Acid → HCID 9872301, compound

HRID 1066521Notes

Reaction equation

HRID 1066521 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]2[N:16]=[C:15]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH:27]([CH3:29])[CH3:28])=[CH:23][N:22]=3)(=[O:20])=[O:19])[C:14]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH3:38])=[C:13]([O:39][CH3:40])[N:12]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].[OH-].[Na+].Cl>>[CH:27]([C:24]1[CH:25]=[CH:26][C:21]([S:18]([NH:17][C:15]2[C:14]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH3:38])=[C:13]([O:39][CH3:40])[N:12]=[C:11]([C:9]3[CH:8]=[CH:7][N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=3)[N:16]=2)(=[O:19])=[O:20])=[N:22][CH:23]=1)([CH3:29])[CH3:28]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9850898HCID 9850898, compound2×

Product 1

HCID 9872301HCID 9872301, compound

Procedure

To a solution of 56.6 mg of 4-[4-(5-isopropyl-pyridine-2-sulfonylamino)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-2-yl]-pyridine-2-carboxylic acid methyl ester, product of example 43, there were added at RT 0.5 ml of 1N NaOH and the solution was stirred for 1 h until the reaction was complete according to TLC analysis. It was then poured into cold diluted HCl and the product was extracted into EtOAc. The organic layer was washed with water, dried over Na2SO4 and the solvent removed in vacuo. The solid residue was washed with ether then dried in a high vacuum to give 4-[4-(5-isopropyl-pyridine-2-sulfonylamino)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-2-yl]-pyridine-2-carboxylic acid as a light yellow crystalline solid. ISN mass spectrum, m/e 550.1 (M−1 calculated for C26H25N5O7S: 550).

Workup

  1. extractionthe product was extracted into EtOAc
  2. washThe organic layer was washed with water
  3. dry with materialdried over Na2SO4
  4. customthe solvent removed in vacuo
  5. washThe solid residue was washed with ether
  6. customthen dried in a high vacuum

Sources & evidence

ORD record
ord-99c9884f70b042619284c822125968de
Source dataset
uspto-grants-2001_06
Patent number
US06242601B1

Reaction notes

Loading…