4-Phenylbutyric Acid → 4-phenylbutyrylamino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one

HRID 481450Notes

Reaction equation

HRID 481450 reaction equation
S(Cl)(Cl)=O.[C:5]1([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.N[C:18]1[CH:34]=[CH:33][C:32]2[C:23]3[NH:24][C:25](=[O:31])[C:26]4[N:27]([CH:28]=[CH:29][N:30]=4)[C:22]=3[CH2:21][C:20]=2[CH:19]=1.C[N:36](C)C=O>ClCCl>[C:5]1([CH2:11][CH2:12][CH2:13][C:14]([NH:36][C:28]2[N:27]3[C:22]4[CH2:21][C:20]5[CH:19]=[CH:18][CH:34]=[CH:33][C:32]=5[C:23]=4[NH:24][C:25](=[O:31])[C:26]3=[N:30][CH:29]=2)=[O:16])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 47754-Phenylbutyric AcidHCID 6228Dimethylformamide2×HCID 24386Thionyl ChlorideHCID 189753948-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one

Product 1

HCID 867529674-phenylbutyrylamino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A few drops of dimethylformamide and then, dropwise, 2.8 ml of thionyl chloride are added to 5 g of 4-phenylbutyric acid, in solution in 60 ml of anhydrous dichloromethane, at a temperature in the region of 20° C. After reacting overnight at the same temperature, the reaction mixture is concentrated to dryness under reduced pressure. The chloride of 4-phenylbutyric acid thus prepared is added dropwise to 1 g of 8-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one, in solution in 75 ml of dimethylformamide, at a temperature in the region of 20° C. The reaction mixture is heated at reflux for 7 hours. The precipitate formed is filtered and recrystallized from dimethylformamide. After filtration, washing with water and then ethyl ether and drying under partial vacuum (1 mm Hg, 0.13 kPa) at 80° C., there is obtained 0.64 g of 8-(4-phenylbutyrylamino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one in the form of an ochre solid which decomposes at 190° C. (Analysis C23H20N4O2.0.63H2O.0.79DMF, % calculated C: 71.86, H: 5.24, N: 14.57, % found C: 71.5, H: 5.1, N: 14.8).

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure
  2. customThe chloride of 4-phenylbutyric acid thus prepared
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux for 7 hours
  5. customThe precipitate formed
  6. filtrationis filtered
  7. customrecrystallized from dimethylformamide
  8. filtrationAfter filtration
  9. washwashing with water
  10. dry with materialethyl ether and drying under partial vacuum (1 mm Hg, 0.13 kPa) at 80° C.

Sources & evidence

ORD record
ord-4d7d68958c5d48b78c56cef8488b338d
Source dataset
uspto-grants-1998_08
Patent number
US05789406

Reaction notes

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