HCID 22609270, compound → HCID 22609235, compound

HRID 2306574Notes

Reaction equation

HRID 2306574 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]1[C:15]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[N:16][N:17]=[C:10]1[N:9]([CH2:23]/[CH:24]=[CH:25]/[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:8]2=[O:32])(=O)C>Cl>[NH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]1[C:15]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)=[N:16][N:17]=[C:10]1[N:9]([CH2:23]/[CH:24]=[CH:25]/[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:8]2=[O:32]

Participants

3

Reactant 1

HCID 22609270HCID 22609270, compound

Product 1

HCID 22609235HCID 22609235, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In a 20 ml balloon flask, we resuspend 0.2 g (0.46 mmol) of 7-acetamido-4-[(E)-3-phenylallyl]-1-(pyrrolidin-1-yl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one (describe example 222) in 5 ml of 6N hydrochloric acid solution and heat by reflux, under shaking, for 15 minutes. After cooling down, the obtained solution is alkalinized by soda solution, extracted 3 times by methylene chloride. The joined organic phases are washed with a NaCl-saturated solution, dried on Na2SO4 then evaporated under vacuum. The crude product (0.12 g) is recrystallized in ethanol to give 0.08 g of the pure compound from example 223.

Workup

  1. customIn a 20 ml balloon flask, we resuspend
  2. temperatureby reflux
  3. temperatureAfter cooling down
  4. extractionextracted 3 times by methylene chloride
  5. washThe joined organic phases are washed with a NaCl-saturated solution
  6. customdried on Na2SO4
  7. customthen evaporated under vacuum
  8. customThe crude product (0.12 g) is recrystallized in ethanol

Sources & evidence

ORD record
ord-315d4e52087d4d4bb719e369ccbe49d7
Source dataset
uspto-grants-2004_12
Patent number
US06828315B1

Reaction notes

Loading…