Water → 10-(3-phenylureido)-5H,10H-imidazo[1,2-a]-indeno[1,2-e]pyrazin-4-one

HRID 1290769Notes

Reaction equation

HRID 1290769 reaction equation
Cl.[NH2:2][CH:3]1[C:15]2[N:14]3[CH:16]=[CH:17][N:18]=[C:13]3[C:12](=[O:19])[NH:11][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2.C(N(CC)CC)C.[C:27]1([N:33]=[C:34]=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CN(C)C=O.CS(C)=O>[C:27]1([NH:33][C:34](=[O:35])[NH:2][CH:3]2[C:15]3[N:14]4[CH:16]=[CH:17][N:18]=[C:13]4[C:12](=[O:19])[NH:11][C:10]=3[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]2=3)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 1897547210-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride

Product 1

HCID 1891815410-(3-phenylureido)-5H,10H-imidazo[1,2-a]-indeno[1,2-e]pyrazin-4-oneYield 44.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

To a suspension of 0.92 g of 10-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride in 20 ml of anhydrous dimethylformamide, maintained under a nitrogen atmosphere at a temperature in the region of 20° C., are added 1.1 g of triethylamine followed, dropwise over 10 minutes, by a solution of 1.25 g of phenyl isocyanate in 2 ml of anhydrous dimethylformamide and the mixture is stirred for 2 hours at the same temperature. The insoluble material formed is separated out by filtration, washed twice with 2 ml in total of dimethylformamide and dried under reduced pressure (5 mmHg; 0.65 kPa) at 100° C. The product obtained (0.9 g) is dissolved in 15 ml of dimethyl sulphoxide and, after addition of 15 ml of distilled water, the solution is stirred for 2 hours at a temperature in the region of 20° C. The insoluble material formed is separated out by filtration, washed twice with 2 ml in total of distilled water and dried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 0.53 g of 10-(3-phenylureido)-5H,10H-imidazo[1,2-a]-indeno[1,2-e]pyrazin-4-one is thus obtained, decomposing without melting above 260° C. [N.M.R. spectrum: [200 MHz; (CD3)2SO d6 ; δ in ppm]: 6.10 (d, J=8.5 Hz, 1H: --CH-- 10); 6.91 (d, J=8.5 Hz, 1H: --NHCO-- at 10); 7.00 (t, J=7.5 Hz, 1H: --H at 4 of the phenylcarbamoyl); 7.31 (t, J=7.5 Hz, 2H: --H at 3 and --H at 5 of the phenylcarbamoyl); 7.38 and 7.48 (2t broad, J=8 Hz, 1H each: --H7 and --H8); 7.52 (d, J=7.5 Hz, 2H: --H at 2 and --H at 6 of the phenylcarbamoyl); 7.60 and 7.85 (2s, 1H each: --H of the imidazole); 7.62 and 7.88 (2d broad, J=8 Hz, 1H each: --H6 and --H9); 8.68 (s, 1H: Ar--NO--CO); 12.50 (broad s, 1H: --CONH-- of the ring)].

Workup

  1. customThe insoluble material formed
  2. customis separated out by filtration
  3. washwashed twice with 2 ml in total of dimethylformamide
  4. customdried under reduced pressure (5 mmHg; 0.65 kPa) at 100° C
  5. customThe product obtained (0.9 g)
  6. stirringthe solution is stirred for 2 hours at a temperature in the region of 20° C
  7. customThe insoluble material formed
  8. customis separated out by filtration
  9. washwashed twice with 2 ml in total of distilled water
  10. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C

Sources & evidence

ORD record
ord-6fd358a81c5e49c0bd1bc1969861f748
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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