Sodium Hydroxide → HCID 86758347, compound

HRID 2229196Notes

Reaction equation

HRID 2229196 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10]CC)=[O:9])=[C:4]([CH2:15][C:16]2[N:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]3=[N:18][C:17]=2[CH2:25][N:26]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[C:36]([O:42][CH3:43])[C:35]=2[Cl:44])[C:27]([CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[O:28])[CH:3]=1.[OH-].[Na+]>CO>[ClH:44].[Br:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([CH2:15][C:16]2[N:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]3=[N:18][C:17]=2[CH2:25][N:26]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[C:36]([O:42][CH3:43])[C:35]=2[Cl:44])[C:27]([CH2:29][CH2:30][CH:31]([CH3:32])[CH3:33])=[O:28])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18466890HCID 18466890, compound

Product 1

HCID 86758347HCID 86758347, compoundYield 109.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 240 mg (0.35 mmol) ethyl 2-{4-bromo-2-[(2-{[(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carbonylamino]methyl}(imidazolo[1,2-a]pyridin-3-yl))methyl]phenoxy}acetate in 4 mL methanol is treated with 55 mg (1.3 mmol) sodium hydroxide. The solution is stirred at room temperature for 3 hr and the solvent removed in vacuo. The residue is redissolved in 5 mL dichloromethane and acidified with 1M hydrochloric acid in ether. The solvent is removed in vacuo and 5 mL dichloromethane is added. The solution is filtered through Celite and the filtrate treated with excess IM hydrochloric acid in ether. The solvent is removed in vacuo and the residue triturated with ether to give 133 mg (58%) 2-{4-bromo-2-[(2-{[(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carbonylamino]methyl}(imidazolo[1,2-a]pyridin-3-yl))methyl]phenoxy}acetic acid mono hydrochloride. Mass Spec m/z (M++1) 658.

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue is redissolved in 5 mL dichloromethane
  3. customThe solvent is removed in vacuo and 5 mL dichloromethane
  4. additionis added
  5. filtrationThe solution is filtered through Celite
  6. additionthe filtrate treated with excess IM hydrochloric acid in ether
  7. customThe solvent is removed in vacuo
  8. customthe residue triturated with ether

Sources & evidence

ORD record
ord-dbd5f480598045bc85347a60fc2b99ff
Source dataset
uspto-grants-2002_07
Patent number
US06420365B1

Reaction notes

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