Acetic Anhydride → N-[(4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-9-yl)methyl]acetamide
Reaction equation
[NH2:1][CH2:2][C:3]1[C:4]2[CH2:5][C:6]3[N:11]4[CH:12]=[CH:13][N:14]=[C:10]4[C:9](=[O:15])[NH:8][C:7]=3[C:16]=2[CH:17]=[CH:18][CH:19]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>>[O:15]=[C:9]1[NH:8][C:7]2[C:16]3[CH:17]=[CH:18][CH:19]=[C:3]([CH2:2][NH:1][C:20](=[O:22])[CH3:21])[C:4]=3[CH2:5][C:6]=2[N:11]2[CH:12]=[CH:13][N:14]=[C:10]12Participants
Conditions
- Temperature
- 20 °C
Procedure
A mixture of 1 g of 9-aminomethyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one and 20 ml of acetic anhydride is stirred under an argon atmosphere for 2 hours at a temperature in the region of 20° C. The reaction mixture is filtered and the insoluble material is washed successively with 10 ml of acetic anhydride and two times 40 ml of methyl-tert-butyl ether and then dried under reduced pressure (15 mm Hg; 2 kPa) at 20° C. The white solid is suspended in a mixture of acetone (30 ml) and methanol (5 ml), then filtered and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 60° C. 1.03 g of N-[(4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-9-yl) methyl]acetamide are obtained in the form of a white solid, the melting point of which is greater than 260° C. (Analysis C16H14N402; % Calculated C: 65.30, H: 4.79, N: 19.04; % Found C: 65.20, H: 5.10, N: 19.30).
Workup
- filtrationThe reaction mixture is filtered
- washthe insoluble material is washed successively with 10 ml of acetic anhydride and two times 40 ml of methyl-tert-butyl ether
- customdried under reduced pressure (15 mm Hg; 2 kPa) at 20° C
- additionThe white solid is suspended in a mixture of acetone (30 ml) and methanol (5 ml)
- filtrationfiltered
- customdried under reduced pressure (1 mm Hg; 0.13 kPa) at 60° C
Sources & evidence
- ORD record
- ord-02ef22babb5d4c979cf3328ec579ce38
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06057454
Reaction notes
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