Hydrochloric Acid → HCID 68700893, compound

HRID 646100Notes

Reaction equation

HRID 646100 reaction equation
C([O:3][C:4]([C:6]1[N:7]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH:33]([CH3:35])[CH3:34])=[CH:28][CH:27]=2)[C:8]2[C:13]([CH:14]=1)=[C:12]([NH2:15])[C:11]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=1)=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+].[ClH:38]>C(#N)C>[ClH:38].[NH2:15][C:12]1[C:11]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH:23]([CH3:24])[CH3:25])=[CH:20][CH:21]=2)=[CH:10][CH:9]=[C:8]2[C:13]=1[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[N:7]2[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH:33]([CH3:34])[CH3:35])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68696976HCID 68696976, compound

Product 1

HCID 68700893HCID 68700893, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-amino-1,5-bis(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester (160 mg, 340 nmol; see step (a)), acetonitrile (5 mL), and aqueous NaOH (1M, 2 mL) was heated at reflux for 3 h, and then allowed to cool. The pH was adjusted to 7 with 1 M HCl, and the mixture extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, concentrated, purified by chromatography, and dissolved in Et2O/absolute ethanol (3 mL). 4M HCl (100 μL) in dioxane was added. The precipitate was filtered off, washed with Et2O, and dried to yield the title compound (124 mg, 86%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureto cool
  4. extractionthe mixture extracted with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. custompurified by chromatography
  9. dissolutiondissolved in Et2O/absolute ethanol (3 mL)
  10. addition4M HCl (100 μL) in dioxane was added
  11. filtrationThe precipitate was filtered off
  12. washwashed with Et2O
  13. customdried

Sources & evidence

ORD record
ord-59fe0cfa5df94471beefa534230ee85d
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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