HCID 18790675, compound → HCID 18790679, compound

HRID 1075518Notes

Reaction equation

HRID 1075518 reaction equation
[NH2:1][CH2:2][C:3]1[CH:19]=[CH:18][C:17]2[C:8]3[NH:9][C:10](=[O:16])[C:11]4[N:12]([CH:13]=[CH:14][N:15]=4)[C:7]=3[CH2:6][C:5]=2[CH:4]=1.[N+](C1C=C[C:26]([N:29](C)[C:30](=O)[O-:31])=CC=1)([O-])=O>CN(C)C=O>[CH3:26][NH:29][C:30](=[O:31])[NH:1][CH2:2][C:3]1[CH:19]=[CH:18][C:17]2[C:8]3[NH:9][C:10](=[O:16])[C:11]4[N:12]([CH:13]=[CH:14][N:15]=4)[C:7]=3[CH2:6][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 18790675HCID 18790675, compoundHCID 67066987HCID 67066987, compound

Product 1

HCID 18790679HCID 18790679, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 1 g of 8-aminomethyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one and 1.8 g of 4-nitrophenyl-N-methylcarbamate in 40 ml of dimethylformamide is stirred for 18 hours at a temperature in the region of 20° C. The reaction mixture is filtered and washed with 5 ml of dimethylformamide. The solid is taken up in 25 ml of dimethylformamide and the suspension is heated at 100° C. for 30 minutes. The insoluble material is filtered and washed with 5 ml of dimethylformamide and then with 20 ml of acetone. After drying under reduced pressure (1 mbar) at 60° C., 1.2 g of 8-(3-methylureido)methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one are obtained in the form of a yellow solid, the melting point of which is greater than 260° C. (Analysis; % Calculated C: 62.13, H: 4.89, N: 22.64; % Found C: 62.0, H: 4.5, N: 22.6).

Workup

  1. filtrationThe reaction mixture is filtered
  2. washwashed with 5 ml of dimethylformamide
  3. temperaturethe suspension is heated at 100° C. for 30 minutes
  4. filtrationThe insoluble material is filtered
  5. washwashed with 5 ml of dimethylformamide
  6. customAfter drying under reduced pressure (1 mbar) at 60° C.

Sources & evidence

ORD record
ord-5dd33409ff154edf98b5909312500cd8
Source dataset
uspto-grants-1999_05
Patent number
US05902803

Reaction notes

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