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Dimethylamine → 10-(3-dimethylaminopropyl)-10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

HRID 2393402
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HRID 2393402 반응식
[H-].[Na+].[CH3:3][CH:4]1[C:16]2[N:15]3[CH:17]=[CH:18][N:19]=[C:14]3[C:13](=[O:20])[NH:12][C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2.C[Si](Cl)(C)C.Br[CH2:27][CH2:28][CH2:29]Cl.[CH3:31][NH:32][CH3:33]>CN(C)C=O.C(OCC)C.C(O)(=O)C.O>[CH3:31][N:32]([CH3:33])[CH2:27][CH2:28][CH2:29][C:4]1([CH3:3])[C:16]2[N:15]3[CH:17]=[CH:18][N:19]=[C:14]3[C:13](=[O:20])[NH:12][C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 5

HCID 674DimethylamineHCID 6397ChlorotrimethylsilaneHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 1897544610-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

생성물 1

HCID 1897547410-(3-dimethylaminopropyl)-10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

0.66 g of 80% sodium hydride is added, under an argon atmosphere, to a stirred solution of 0.96 g of 10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one in 50 ml of dimethylformamide. The stirring is continued for 15 minutes at a temperature in the region of 20° C., followed by addition of 0.56 ml of trimethylsilyl chloride and the mixture is left stirring for 30 minutes. 0.44 ml of 1-bromo-3-chloropropane is then added and the stirring is continued for 25 minutes. 7.2 ml of a 2.78N solution of dimethylamine in ethyl ether are then added and the final mixture is left to react for one week at a temperature in the region of 20° C. The reaction mixture is treated with 10 ml of water and 0.5 ml of acetic acid, then concentrated on a rotary evaporator. The evaporation residue is triturated with 60 ml of isopropanol and filtered. The filtrate is concentrated on a rotary evaporator and the crude product is first purified by chromatography on a column of silica (100 g), eluting under a pressure of 0.5 bar with a mixture of chloroform, methanol and 28% aqueous ammonia (48/6/1 by volume). The product obtained (0.7 g) is then purified by treatment with 0.07N hydrochloric acid (27 ml), washing of the aqueous phase with dichloromethane (2×20 ml), basifying of the aqueous phase using concentrated sodium hydrogen carbonate solution and extraction of the alkaline phase with dichloromethane (3×25 ml) and then with chloroform (50 ml). The organic phases are combined, dried over magnesium sulphate, filtered and evaporated on a rotary evaporator. The evaporation residue is triturated with 30 ml of isopropyl ether, filtered and the solid obtained is dried at 60° C. under vacuum (1 mmHg; 0.13 kPa). 0.28 g of 10-(3-dimethylaminopropyl)-10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is obtained in the form of a white solid melting at about 195° C. (Analysis, % calculated C: 70.78, H: 6.88, N: 17.38, O: 4.96, % found C: 70.5, H: 7.3, N: 16.8).

후처리

  1. waitthe mixture is left
  2. waitthe stirring is continued for 25 minutes
  3. customto react for one week at a temperature in the region of 20° C
  4. concentrationconcentrated on a rotary evaporator
  5. customThe evaporation residue is triturated with 60 ml of isopropanol
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated on a rotary evaporator
  8. customthe crude product is first purified by chromatography on a column of silica (100 g)
  9. washeluting under a pressure of 0.5 bar with a mixture of chloroform, methanol and 28% aqueous ammonia (48/6/1 by volume)
  10. customThe product obtained (0.7 g)
  11. customis then purified by treatment with 0.07N hydrochloric acid (27 ml)
  12. washwashing of the aqueous phase with dichloromethane (2×20 ml)
  13. extractionsodium hydrogen carbonate solution and extraction of the alkaline phase with dichloromethane (3×25 ml)
  14. dry with materialdried over magnesium sulphate
  15. filtrationfiltered
  16. customevaporated on a rotary evaporator
  17. customThe evaporation residue is triturated with 30 ml of isopropyl ether
  18. filtrationfiltered
  19. customthe solid obtained
  20. customis dried at 60° C. under vacuum (1 mmHg; 0.13 kPa)

출처 및 근거

ORD 기록
ord-105d38ecdac54ee38048d87f65d5cb59
출처 데이터셋
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05807859

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