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

HRID 481458Notes

Reaction equation

HRID 481458 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.Cl.[NH2:12][C:13]1[CH:29]=[CH:28][C:27]2[C:18]3[NH:19][C:20](=[O:26])[C:21]4[N:22]([CH:23]=[CH:24][N:25]=4)[C:17]=3[CH2:16][C:15]=2[CH:14]=1.C(N(CC)CC)C>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[NH:12][C:13]2[CH:29]=[CH:28][C:27]3[C:18]4[NH:19][C:20](=[O:26])[C:21]5[N:22]([CH:23]=[CH:24][N:25]=5)[C:17]=4[CH2:16][C:15]=3[CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709554-Fluorophenyl isocyanateHCID 189754908-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one hydrochloride

Product 1

HCID 152930218-[3-(4-fluoro-phenyl)ureido]-5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazine-4-oneYield 54.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1.76 g of 4-fluorophenyl isocyanate in 20 ml of dimethylformamide is added over 30 minutes to a solution of 2 g of 8-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one hydrochloride, 20 ml of dimethylformamide and 1.3 g of triethylamine and stirring is carried out for 12 hours at a temperature in the region of 20° C. The reaction mixture is filtered and the insoluble material is washed with dimethylformamide (2×10 ml) and then with water (3×15 ml) and dried in the air. The crude product is then triturated in 30 ml of dimethylformamide, filtered, washed with water and then with isopropyl ether and dried at 60° C. under vacuum (1 mm Hg, 0.13 kPa). There are obtained 1.5 g of 8-[3-(4-fluoro-phenyl)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: 3.8, N: 19.0).

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe insoluble material is washed with dimethylformamide (2×10 ml)
  3. dry with materialwith water (3×15 ml) and dried in the air
  4. customThe crude product is then triturated in 30 ml of dimethylformamide
  5. filtrationfiltered
  6. washwashed with water
  7. dry with materialwith isopropyl ether and dried at 60° C. under vacuum (1 mm Hg, 0.13 kPa)

Sources & evidence

ORD record
ord-2b9bab19925744528d7393a114e23700
Source dataset
uspto-grants-1998_08
Patent number
US05789406

Reaction notes

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