Triethylamine → 10-nicotinoylamino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

HRID 2393376Notes

Reaction equation

HRID 2393376 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.Cl.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=1>CN(C)C=O.C(O)(C)C.CO>[C:28]([NH: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)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 1897547210-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride

Product 1

HCID 1897544010-nicotinoylamino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-oneYield 32%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 0.6 g of 10-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride in 30 ml of anhydrous dimethylformamide are added successively, at a temperature in the region of 20° C., 0.6 g of triethylamine and 0.42 g of nicotinoyl chloride hydrochloride. The mixture is stirred for 2 hours at the same temperature, the insoluble product formed is removed by filtration and the filtrate is concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 80° C. The product obtained (1.04 g) is suspended for 10 minutes in 20 ml of boiling isopropanol and, after cooling and storing at 5° C. for 1 hour, is isolated by filtration, washed with 1 ml of chilled isopropanol and dried under reduced pressure (1 mmHg; 0.13 kPa) at 60° C. The product obtained (0.43 g) is suspended in 5 ml of methanol, isolated by filtration, washed with 2 ml of methanol and dried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 0.24 g of 10-nicotinoylamino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one are thus obtained, decomposing without melting above 260° C. (NMR spectrum: [200 MHz; (CD3)2SO-d6 ; δ in ppm]: 6.42 (d, J=8.5 Hz, 1H: --CH 10); 7.40 and 7.51 (2 broad t, J=8 Hz, 1H each: --H7 and --H8); 7.58 and 7.92 (2 broad d, J=8 Hz, 1H each: --H6 and --H9); 7.62 and 7.74 (2s, 1H each: --H of the imidazole); 7.62 (dd, J=8.5 and 5 Hz, 1H: --H at 5 of the pyridine); 8.33 (broad d, J=8.5 Hz, 1H: --H at 4 of the pyridine); 8.79 (broad d, J=5 Hz, 1H: --H at 6 of the pyridine); 9.11 (mt, 1H: --H at 2 of the pyridine); 9.38 (d, J=8.5 Hz, 1H: --NHCO-- at 10); 12.63 (broad s, 1H: --CONH of the ring)).

Workup

  1. customthe insoluble product formed
  2. customis removed by filtration
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 80° C
  4. customThe product obtained (1.04 g)
  5. temperatureafter cooling
  6. waitstoring at 5° C. for 1 hour
  7. customis isolated by filtration
  8. washwashed with 1 ml of chilled isopropanol
  9. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 60° C
  10. customThe product obtained (0.43 g)
  11. customisolated by filtration
  12. washwashed with 2 ml of methanol
  13. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C

Sources & evidence

ORD record
ord-a7b33fcde3c74f739be6743b2512136f
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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