HCID 1133837, compound → HCID 178517003, compound

HRID 2297862Notes

Reaction equation

HRID 2297862 reaction equation
C(O[CH:4]=[C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]3[N:16]=[CH:15][S:14][C:12]3=2)[NH:7][C:6]1=[O:17])C.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(O)C>[O:17]=[C:6]1[C:5](=[CH:4][NH:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=3)(=[O:27])=[O:26])=[CH:21][CH:20]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]3[N:16]=[CH:15][S:14][C:12]3=2)[NH:7]1

Participants

4

Reactant 2

HCID 1133837HCID 1133837, compoundHCID 539908078-[Ethoxymethylidene]-6H-[1,3]thiazolo[5,4-e]indol-7-one

Product 1

HCID 178517003HCID 178517003, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

To a test tube (20 mm by 150 mm) was added a magnetic stir bar, 8-[ethoxymethylidene]-6H-[1,3]thiazolo[5,4-e]indol-7-one (0.123 gram, 0.5 mmol), 4-amino-N-(4-pyridinylmethyl)benzenesulfonamide (0.132 gram, 0.5 mmol) and 95% ethanol (5 milliliters). The reaction mixture was sealed with a rubber septum (14/22) and vented with a 3-inch 18-gauge hypodermic needle. The reaction vessel was placed in an oil bath at room temperature with stirring, and the temperature of the oil bath was then raised to 78° C. and maintained at that temperature for approximately 24 hours. The reaction vessel was removed from the oil bath and allowed to cool until warm to the touch. The resulting precipitate was collected by suction filtration. The solid was washed with excess 95% ethanol and collected by suction filtration. The resultant solid was dried under vacuum for two hours at 40° C. The solid was allowed to cool to yield 52 mg (11%) of the title compound. MS (M+H)=464.

Workup

  1. additionTo a test tube (20 mm by 150 mm) was added a magnetic stir bar
  2. customThe reaction vessel was placed in an oil bath at room temperature
  3. temperaturemaintained at that temperature for approximately 24 hours
  4. customThe reaction vessel was removed from the oil bath
  5. temperatureto cool
  6. temperatureuntil warm to the touch
  7. filtrationThe resulting precipitate was collected by suction filtration
  8. washThe solid was washed with excess 95% ethanol
  9. filtrationcollected by suction filtration
  10. customThe resultant solid was dried under vacuum for two hours at 40° C
  11. temperatureto cool

Sources & evidence

ORD record
ord-9af3c93542754058a6314579cf851ea0
Source dataset
uspto-grants-2002_12
Patent number
US06492398B1

Reaction notes

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