Methyl Isocyanate → ethyl 8-(3-methylureido)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate

HRID 1604

Reaction equation

HRID 1604 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[NH2:5][C:6]1[CH:27]=[CH:26][C:25]2[C:11]3[NH:12][C:13](=[O:24])[C:14]4[N:15]([CH:16]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=4)[C:10]=3[CH2:9][C:8]=2[CH:7]=1>CN(C)C=O>[CH3:1][NH:2][C:3](=[O:4])[NH:5][C:6]1[CH:27]=[CH:26][C:25]2[C:11]3[NH:12][C:13](=[O:24])[C:14]4[N:15]([CH:16]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=4)[C:10]=3[CH2:9][C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 19691053ethyl 8-amino-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate

Product 1

HCID 19691068ethyl 8-(3-methylureido)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.44 ml of methyl isocyanate is added dropwise with stirring to a suspension of 580 mg of ethyl 8-amino-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in 10 ml of dimethylformamide and stirring is continued for 12 hours at a temperature close to 20° C. The reaction mixture is then filtered, rinsed with dimethylformamide and dried at 35° C. under vacuum (1 mm Hg; 0.13 kPa). 320 mg of ethyl 8-(3-methylureido)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate are obtained as a dihydrate in the form of a beige solid melting above 260° C. (analysis % calculated C: 53.59, H: 5.25, N: 17.36; % found C: 53.2, H: 4.7, N: 17.7).

Workup

  1. customclose to 20° C
  2. filtrationThe reaction mixture is then filtered
  3. washrinsed with dimethylformamide
  4. customdried at 35° C. under vacuum (1 mm Hg; 0.13 kPa)

Sources & evidence

ORD record
ord-285176e937a841c4943a04d3364e6c62
Source dataset
uspto-grants-1998_03
Patent number
US05726175

Linked notes

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