Dimethylcarbamoyl Chloride → HCID 19066057, compound

HRID 481454Notes

Reaction equation

HRID 481454 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[NH2:7][C:8]1[CH:24]=[CH:23][C:22]2[C:13]3[NH:14][C:15](=[O:21])[C:16]4[N:17]([CH:18]=[CH:19][N:20]=4)[C:12]=3[CH2:11][C:10]=2[CH:9]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[OH2:4].[OH2:21].[CH3:1][N:2]([CH3:6])[C:3](=[O:4])[NH:7][C:8]1[CH:24]=[CH:23][C:22]2[C:13]3[NH:14][C:15](=[O:21])[C:16]4[N:17]([CH:18]=[CH:19][N:20]=4)[C:12]=3[CH2:11][C:10]=2[CH:9]=1

Participants

5

Reactant 2

HCID 6598Dimethylcarbamoyl Chloride2×HCID 189753948-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one

Product 1

HCID 19066057HCID 19066057, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

1.2 ml of dimethylcarbamoyl chloride are added dropwise to 1.5 g of 8-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one and 0.15 g of 4-dimethylaminopyridine in 45 ml of pyridine. After reacting for 5 hours at a temperature in the region of 20° C., 1.2 ml of dimethylcarbamoyl chloride are again added. The reaction is continued overnight at the same temperature and the reaction mixture is then heated at 50° C. for 1 hour. After cooling, the insoluble material is filtered, washed with water and dried. The solid thus obtained is recrystallized from dimethylformamide, washed with water and then dried under partial vacuum (1 mm Hg, 0.13 kPa) at 50° C. There is obtained 0.3 g of 8-(3,3-dimethylureido)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one dihydrate in the form of a pink solid, the melting point of which is greater than 260° C. (Analysis C16H15N5 O2.2H2O, % calculated C: 62.13, H: 4.89, N: 22.64, % found C: 62.2, H: 4.6, N: 22.4).

Workup

  1. additionare again added
  2. temperatureAfter cooling
  3. filtrationthe insoluble material is filtered
  4. washwashed with water
  5. customdried
  6. customThe solid thus obtained
  7. customis recrystallized from dimethylformamide
  8. washwashed with water
  9. customdried under partial vacuum (1 mm Hg, 0.13 kPa) at 50° C

Sources & evidence

ORD record
ord-0d1b27fe488b4f87b0857a2f0c95a635
Source dataset
uspto-grants-1998_08
Patent number
US05789406

Reaction notes

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