Sodium Hydroxide → HCID 21254645, compound

HRID 636526Notes

Reaction equation

HRID 636526 reaction equation
C([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([NH:16][CH2:17][C:18]([N:20]([C:22]2[C:23]([Cl:43])=[C:24]([C:39]([Cl:42])=[CH:40][CH:41]=2)[CH2:25][O:26][C:27]2[C:35]3[N:34]=[C:33]([O:36][CH3:37])[N:32]([CH3:38])[C:31]=3[CH:30]=[CH:29][CH:28]=2)[CH3:21])=[O:19])=[O:15])=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[C:4]([C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([NH:16][CH2:17][C:18]([N:20]([C:22]2[C:23]([Cl:43])=[C:24]([C:39]([Cl:42])=[CH:40][CH:41]=2)[CH2:25][O:26][C:27]2[C:35]3[N:34]=[C:33]([O:36][CH3:37])[N:32]([CH3:38])[C:31]=3[CH:30]=[CH:29][CH:28]=2)[CH3:21])=[O:19])=[O:15])=[CH:8][CH:7]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21254740HCID 21254740, compound

Product 1

HCID 21254645HCID 21254645, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-[3-[N-[(E)-3-(6-ethoxycarbonylpyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methoxy-1-methyl-1H-benzimidazole (304 mg) in ethanol was added 1N sodium hydroxide solution (0.5 ml), and the mixture was stirred for 1.5 hours at ambient temperature. The solvent was removed, water was added to the residue. The mixture was adjusted to pH 4 with 1N hydrochloric acid and extracted with chloroform. The extract was dried and evaporated in vacuo. Acetonitrile was added to the residue, and the residue was collected by filtration to give 4-[3-[N-[(E)-3-(6-carboxypyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methoxy-1-methyl-1H-benzimidazole (195 mg).

Workup

  1. customThe solvent was removed
  2. additionwater was added to the residue
  3. extractionextracted with chloroform
  4. customThe extract was dried
  5. customevaporated in vacuo
  6. additionAcetonitrile was added to the residue
  7. filtrationthe residue was collected by filtration

Sources & evidence

ORD record
ord-c70433ae70e3433d94ccc2335647540d
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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