Dimethylformamide → HCID 178518649, compound

HRID 2393384Notes

Reaction equation

HRID 2393384 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=[C:7]2[C:19]3[N:18]4[CH:20]=[CH:21][N:22]=[C:17]4[C:16](=[O:23])[NH:15][C:14]=3[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)[N:3]=[CH:2]1.CN(C)C=O>[Pd].C(O)(=O)C>[NH:1]1[CH:5]=[C:4]([CH2:6][CH:7]2[C:19]3[N:18]4[CH:20]=[CH:21][N:22]=[C:17]4[C:16](=[O:23])[NH:15][C:14]=3[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)[N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 178518570HCID 178518570, compound

Product 1

HCID 178518649HCID 178518649, compoundYield 14.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

The process is performed as in Example 3 but starting with 1.1 g of 10-(4-imidazolylmethylene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 250 ml of dimethylformamide, 5 ml of acetic acid and 0.1 g of 10% palladium-on-charcoal. After evaporation of the solvents, the crude product is purified by chromatography on a column of silica (100 g partially deactivated with 3% water), eluting with a mixture of chloroform, methanol and 28% aqueous ammonia (24/6/1 by volume). A pale yellow solid is obtained which is triturated with 20 ml of water, filtered, washed with 20 ml of ethyl ether and dried at 80° C. under vacuum (2 mmHg; 0.26 kPa) to give 0.16 g of 10-(4-imidazolylmethyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one in the form of an off-white solid melting above 260° C. (Analysis, % calculated C: 67.32, H: 4.32, N: 23.09, O: 5.27, % found C: 67.7, H: 4.2, N: 22.6).

Workup

  1. customAfter evaporation of the solvents
  2. customthe crude product is purified by chromatography on a column of silica (100 g
  3. washeluting with a mixture of chloroform, methanol and 28% aqueous ammonia (24/6/1 by volume)
  4. customA pale yellow solid is obtained which
  5. customis triturated with 20 ml of water
  6. filtrationfiltered
  7. washwashed with 20 ml of ethyl ether
  8. customdried at 80° C. under vacuum (2 mmHg; 0.26 kPa)

Sources & evidence

ORD record
ord-dfd1d5c5dc134a2993ebb3cf33300bda
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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