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

HRID 481449Notes

Reaction equation

HRID 481449 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.C(N(CC)CC)C.[C:27]([N:31]=[C:32]=[O:33])([CH3:30])([CH3:29])[CH3:28].CN(C)C=O>O>[C:27]([NH:31][C:32](=[O:33])[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)([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 189754908-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one hydrochloride

Product 1

HCID 190660208-(3-tert-butylureido)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The preparation is carried out as in Example 7, from 1.2 g of 8-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one hydrochloride, 1.8 ml of triethylamine, 2 times 0.6 ml of tert-butyl isocyanate and 25 ml of dimethylformamide. After addition of 100 ml of distilled water to the reaction mixture, the precipitate formed is filtered and recrystallized from dimethylformamide. The solid thus obtained is washed with water, then with ethyl ether and dried under reduced pressure (1 mm Hg, 0.13 kPa) at 80° C. There is obtained 0.31 g of 8-(3-tert-butylureido)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one in the form of a brown solid, the melting point of which is greater than 260° C. (Analysis C18H19N5O2 0.83H2 0.0.03DMF, % calculated C: 64.08, H: 5.68, N: 20.76, % found C: 63.7, H: 5.9, N: 20.6).

Workup

  1. customthe precipitate formed
  2. filtrationis filtered
  3. customrecrystallized from dimethylformamide
  4. customThe solid thus obtained
  5. washis washed with water
  6. dry with materialwith ethyl ether and dried under reduced pressure (1 mm Hg, 0.13 kPa) at 80° C

Sources & evidence

ORD record
ord-bea11520e20143be965b0c95972157a7
Source dataset
uspto-grants-1998_08
Patent number
US05789406

Reaction notes

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