Ammonia → HCID 18790622, compound

HRID 1107034Notes

Reaction equation

HRID 1107034 reaction equation
C([N:3](CC)CC)C.Cl.[O:9]=[C:10]1[NH:15][C:14]2[C:16]3[CH:17]=[CH:18][C:19]([CH2:23][C:24](O)=[O:25])=[CH:20][C:21]=3[CH2:22][C:13]=2[N:12]2[CH:27]=[CH:28][N:29]=[C:11]12.C(N1C=CN=C1)(N1C=CN=C1)=O.N>CN(C)C=O>[O:9]=[C:10]1[NH:15][C:14]2[C:16]3[CH:17]=[CH:18][C:19]([CH2:23][C:24]([NH2:3])=[O:25])=[CH:20][C:21]=3[CH2:22][C:13]=2[N:12]2[CH:27]=[CH:28][N:29]=[C:11]12

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 70272848HCID 70272848, compound

Product 1

HCID 18790622HCID 18790622, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

1.21 ml of triethylamine are added to a suspension, under nitrogen, of 2.9 g of [4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-8-yl]acetic acid hydrochloride and 108 ml of dimethylformamide. After stirring for 30 minutes at a temperature in the region of 20° C., 3.5 g of 1,1'-carbonyldiimidazole are added to the reaction mixture and stirring is continued for 2 hours at a temperature in the region of 20° C. The reaction mixture is then cooled to -10° C. and a stream of gaseous ammonia is passed into the mixture for 15 minutes. After returning to a temperature in the region of 20° C., the reaction mixture is concentrated to dryness under reduced pressure. The evaporation residue is taken up in 100 ml of distilled water and the suspended solid is filtered, washed with water and then dissolved in 125 ml of dimethyl sulphoxide. The addition of 250 ml of acetone to the solution causes the appearance of a precipitate which is collected by filtration, washed with acetone and dried under reduced pressure (1 mbar) at 60° C. 1.1 g of [4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-8-yl]acetamide are thus obtained in the form of a beige solid with a melting point greater than 260° C. (Analysis; % Calculated C: 64.28, H: 4.32, N: 19.99, O: 11.42; % Found C: 63.9, H: 4.3, N: 19.8, O: 10.9).

Workup

  1. additionare added to the reaction mixture
  2. customAfter returning to a temperature in the region of 20° C.
  3. concentrationthe reaction mixture is concentrated to dryness under reduced pressure
  4. filtrationthe suspended solid is filtered
  5. washwashed with water
  6. dissolutiondissolved in 125 ml of dimethyl sulphoxide
  7. additionThe addition of 250 ml of acetone to the solution
  8. filtrationis collected by filtration
  9. washwashed with acetone
  10. customdried under reduced pressure (1 mbar) at 60° C

Sources & evidence

ORD record
ord-051eb3fc68ef416492f1037362b6aba7
Source dataset
uspto-grants-2000_05
Patent number
US06057454

Reaction notes

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