Dimethylformamide → 8-[3-(2-fluorophenyl)ureido]-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one

HRID 481460Notes

Reaction equation

HRID 481460 reaction equation
Cl.[NH2:2][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.CN(C)C=O.[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]=[C:33]=[O:34]>C(N(CC)CC)C>[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][C:33](=[O:34])[NH: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

5

Reactant 3

HCID 6228DimethylformamideHCID 855882-Fluorophenyl isocyanateHCID 189754908-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one hydrochloride

Product 1

HCID 190660348-[3-(2-fluorophenyl)ureido]-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-oneYield 36.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The preparation is carried out as in Example 36 but from 2 g of 8-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one hydrochloride, 40 ml of dimethylformamide, 1.3 g of triethylamine and 1.76 g of 2-fluorophenyl isocyanate. There is obtained 1 g of 8-[3-(2-fluorophenyl)ureido]-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one in the form of a beige solid melting above 260° C. (Analysis, % calculated C: 64.00, H: 3.76, F: 5.06, N: 18.66, O: 8.52, % found C: 64.0, H: 3.5, F: 4.6, N: 18.6).

Sources & evidence

ORD record
ord-a2f2ddba4313488ea33571e80828dbb4
Source dataset
uspto-grants-1998_08
Patent number
US05789406

Reaction notes

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