Hydrochloric Acid → HCID 66657644, compound

HRID 420948Notes

Reaction equation

HRID 420948 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][N:17]=3)[CH:13]=2)[N:8]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH:30]([CH3:32])[CH3:31])=[CH:25][CH:24]=2)[C:7]=1[CH2:33][C:34]([O:36]CC)=[O:35])=[O:5])[CH3:2].[OH-].[Na+].Cl>CCO>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][N:17]=3)[CH:13]=2)[N:8]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH:30]([CH3:32])[CH3:31])=[CH:25][CH:24]=2)[C:7]=1[CH2:33][C:34]([OH:36])=[O:35])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66658102HCID 66658102, compound

Product 1

HCID 66657644HCID 66657644, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(5-aminopyridin-2-yloxy)-2-ethoxycarbonylmethyl-1-(4-isopropoxyphenyl)indole-3-carboxylic acid ethyl ester (185 mg, 0.36 mmol; see step (b) above), NaOH (aq, 2 M, 2 mL) and EtOH (15 mL) was stirred at rt for 20 h, acidified to pH 2 with HCl (aq, 1 M) and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried (Na2SO4), concentrated and purified by chromatography to give the sub-title compound. Yield 130 mg (74%).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-64943a2669a045c4a2d684231967b759
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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