HCID 18975435, compound → HCID 70202500, compound

HRID 2393369Notes

Reaction equation

HRID 2393369 reaction equation
[C:1]([O:5][C:6]([CH:8]([CH:10]1[C:22]2[N:21]3[CH:23]=[CH:24][N:25]=[C:20]3[C:19](=[O:26])[NH:18][C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]1=2)O)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CN(C)C=O>[C:1]([O:5][C:6]([CH:8]=[C:10]1[C:22]2[N:21]3[CH:23]=[CH:24][N:25]=[C:20]3[C:19](=[O:26])[NH:18][C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]1=2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 18975435HCID 18975435, compound

Product 1

HCID 70202500HCID 70202500, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.85 g of 10-(1-tert-butoxycarbonyl-1-hydroxymethyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one are heated to 90°-100° C. in 300 ml of dimethylformamide, filtered immediately and 150 ml of methanol and 200 ml of water are added to the filtrate, which is left overnight at a temperature in the region of 5° C. The crystals formed are filtered off, washed with 20 ml of water and dried at 80° C. under vacuum (2 mmHg; 0.26 kPa) to give 3.4 g of 10-(tert-butoxycarbonylmethylene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one in the form of a red solid melting above 260° C. (Analysis, % calculated C: 68.05, H: 5.11, N: 12.53, O: 14.31, % found C: 68.0, H: 5.6, N: 12.5, O: 14.3).

Workup

  1. filtrationfiltered immediately
  2. addition150 ml of methanol and 200 ml of water are added to the filtrate, which
  3. customThe crystals formed
  4. filtrationare filtered off
  5. washwashed with 20 ml of water
  6. customdried at 80° C. under vacuum (2 mmHg; 0.26 kPa)

Sources & evidence

ORD record
ord-851b3d67e4a54fcd801657f3e3df91a6
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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