Hydrochloric Acid → HCID 9899972, compound

HRID 1795868Notes

Reaction equation

HRID 1795868 reaction equation
C([NH:4][C:5]1[CH:23]=[CH:22][C:8]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([NH2:19])=[C:13]3[C:20]#[N:21])=[CH:7][CH:6]=1)(=O)C.O.Cl.C([O-])(O)=O.[Na+]>CO>[NH2:4][C:5]1[CH:23]=[CH:22][C:8]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([NH2:19])=[C:13]3[C:20]#[N:21])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 9815029HCID 9815029, compound

Product 1

HCID 9899972HCID 9899972, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 5-(4-acetylaminophenoxy)-2-amino-1H-indole-3-carbonitrile (Example 14)(306 mg; 1 mmol) in MeOH (10 ml) was treated with water (2 ml) and conc. HCl (1 ml) and the mixture heated under reflux for 30 hours. After cooling the mixture was poured into sat. aqueous NaHCO3 and extracted with EtOAc. The organic phase was washed with brine and dried over MgSO4. The residue was purified by flash chromatography eluting with increasingly polar mixtures of EtOAc/hexanes (80 to 100% EtOAc) to give 5-(4-aminophenoxy)-2-amino-1H-indole-3-carbonitrile as a pale beige solid (251 mg).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 30 hours
  3. temperatureAfter cooling the mixture
  4. extractionextracted with EtOAc
  5. washThe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. customThe residue was purified by flash chromatography
  8. washeluting
  9. temperaturewith increasingly polar mixtures of EtOAc/hexanes (80 to 100% EtOAc)

Sources & evidence

ORD record
ord-7974dccf90ff4569907f1f5c148ea1ff
Source dataset
uspto-grants-2006_04
Patent number
US07030123B2

Reaction notes

Loading…