Water → HCID 59189801, compound

HRID 216639Notes

Reaction equation

HRID 216639 reaction equation
Cl.[NH2:2]O.C([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]([C:23]#[N:24])[C:20]([NH2:22])=[O:21])(=O)C1C=CC=CC=1.O.C(O[C:30](=[O:32])C)(=O)C.[N:33]1[CH:38]=CC=CC=1>C(O)C>[NH2:2][C:30]([NH:24][C:23]1[NH:12][C:13]2[C:14]([C:19]=1[C:20]([NH2:22])=[O:21])=[CH:15][CH:16]=[C:17]([C:38]#[N:33])[CH:18]=2)=[O:32]

Participants

7

Reactant 5

HCID 962Water2×HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 16122022HCID 16122022, compound2×

Product 1

HCID 59189801HCID 59189801, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Hydroxylamine hydrochloride (28 mg, 0.40 mmol) was added to a solution of 2-aminocarbonylamino-6-formylindole-3-carboxamide (Compound 17-1, 40 mg, 0.16 mmol) in anhydrous ethanol (2 mL), the mixture was stirred at 70° C. for 2.5 hours. Water (5 mL) was added to the reaction mixture, and the whole was extracted with ethyl acetate (10 mL). The organic layer was washed with brine (5 mL), and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resultant solid was washed with diethyl ether (2 mL), and dried under reduced pressure. Acetic anhydride (18 μL, 0.19 mmol) was added to a solution of the resultant solid in anhydrous pyridine (1 mL), and the mixture was stirred at 100° C. for 4 hours. Water (3 mL) was added to the reaction mixture, and the whole was extracted with ethyl acetate (10 mL). The organic layer was washed with brine (5 mL), and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resultant solid was washed with diethyl ether (2 mL) and dried under reduced pressure to give the title compound (5.0 mg) as a brown solid (yield 12%)

Workup

  1. extractionthe whole was extracted with ethyl acetate (10 mL)
  2. washThe organic layer was washed with brine (5 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter the solvent was evaporated under reduced pressure
  5. washthe resultant solid was washed with diethyl ether (2 mL)
  6. customdried under reduced pressure
  7. stirringthe mixture was stirred at 100° C. for 4 hours
  8. extractionthe whole was extracted with ethyl acetate (10 mL)
  9. washThe organic layer was washed with brine (5 mL)
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customAfter the solvent was evaporated under reduced pressure
  12. washthe resultant solid was washed with diethyl ether (2 mL)
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-2b12f57adbf04a9782c2ec05f35c25c7
Source dataset
uspto-grants-2012_06
Patent number
US08193237B2

Reaction notes

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