Sodium Hydroxide → HCID 21200276, compound

HRID 1066523Notes

Reaction equation

HRID 1066523 reaction equation
[Na].C[O:3][C:4]([C:6]1[CH:11]=[C:10]([C:12]2[N:17]=[C:16]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([CH3:30])=[CH2:29])=[CH:24][N:23]=3)(=[O:21])=[O:20])[C:15]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[O:38][CH3:39])=[C:14]([O:40][CH3:41])[N:13]=2)[CH:9]=[CH:8][N:7]=1)=N.[OH-:42].[Na+]>CO>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([S:19]([NH:18][C:16]2[C:15]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[O:38][CH3:39])=[C:14]([O:40][CH3:41])[N:13]=[C:12]([C:10]3[CH:9]=[CH:8][N:7]=[C:6]([C:4]([OH:42])=[O:3])[CH:11]=3)[N:17]=2)(=[O:20])=[O:21])=[N:23][CH:24]=1)([CH3:30])=[CH2:29]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 69287910HCID 69287910, compound

Product 1

HCID 21200276HCID 21200276, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.1 g of 4-[4-(5-isopropenyl-pyridine-2-sulfonylamino)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-2-yl]-pyridine-2-carboximidic acid methyl ester sodium salt, product of example 66 b), in MeOH (10 ml) were treated at RT with 1.8 ml 1N NaOH and the solution was stirred for 26 h at RT. After this time further 1.8 ml 1N NaOH were added and stirring was continued for further 20 h until the reaction was complete according to HPLC analysis. The solution was concentrated then poured into diluted aqueous HCl, the product was extracted into AcOEt. The organic layer was washed with water, dried over Na2SO4 and concentrated in vacuo. The crystalline precipitate that had formed was collected under suction and washed with ether to give 4-[4-(5-isopropenyl-pyridine-2-sulfonylamino)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-2-yl]-pyridine-2-carboxylic acid as light yellow crystals. ISN mass spectrum, m/e 548 (M−1 calculated for C26H23N5O7S: 548).

Workup

  1. stirringstirring
  2. waitwas continued for further 20 h until the reaction
  3. concentrationThe solution was concentrated
  4. additionthen poured into diluted aqueous HCl
  5. extractionthe product was extracted into AcOEt
  6. washThe organic layer was washed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crystalline precipitate that had formed
  10. customwas collected under suction
  11. washwashed with ether

Sources & evidence

ORD record
ord-693bf648fc6741a2ab67ceded2f92f86
Source dataset
uspto-grants-2001_06
Patent number
US06242601B1

Reaction notes

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