Dimethylacetamide → N-methyl-6-[(1-tosyl-1H-imidazol-4-yl)carbonyl]-2-naphthamide

HRID 922724노트

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HRID 922724 반응식
[OH:1][CH:2]([C:17]1[N:18]=[CH:19][N:20]([S:22]([C:25]2[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:21]=1)[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]([NH:15][CH3:16])=[O:14])[CH:7]=[CH:6]2.CN(C)C(=O)C>[O-2].[O-2].[Mn+4].C(OCC)(=O)C>[CH3:16][NH:15][C:13]([C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:2]([C:17]3[N:18]=[CH:19][N:20]([S:22]([C:25]4[CH:26]=[CH:27][C:28]([CH3:29])=[CH:30][CH:31]=4)(=[O:23])=[O:24])[CH:21]=3)=[O:1])[CH:4]=2)[CH:9]=1)=[O:14]

참가 물질

5

반응물 2

HCID 31374DimethylacetamideHCID 711172346-(hydroxy(1-tosyl-1H-imidazol-4-yl)methyl)-N-methyl-2-naphthamide

생성물 1

HCID 86715406N-methyl-6-[(1-tosyl-1H-imidazol-4-yl)carbonyl]-2-naphthamide수율 79.8%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

6-(Hydroxy(1-tosyl-1H-imidazol-4-yl)methyl)-N-methyl-2-naphthamide (8.2 g, 18.8 mmol) and manganese dioxide (14.7 g, 169.1 mmol) were added to N,N-dimethylacetamide (70 mL), and the mixture was stirred at 60° C. for 7 hr. The insoluble material was filtered off from the obtained reaction mixture at 60° C., and washed with N,N-dimethylacetamide (33 mL). The filtrate and washing were combined, and cooled to 40° C., water (49 mL) was added dropwise thereto, and the mixture was stirred at the same temperature for 0.5 hr or more, and then at room temperature for 1 hr or more to give crystals. The obtained crystals were collected by filtration, and washed with water (51 mL) to give wet crystals. The obtained wet crystals were dried under reduced pressure at an outside temperature of 50° C. to give crude crystals (6.6 g). Ethyl acetate (66 mL) were warmed to 40° C., and the crude crystals (6.6 g) were added thereto. The obtained mixture was warmed to 50° C., and stirred for 0.5 hr or more, and 13 mL of the solvent was evaporated under reduced pressure. The obtained residue was allowed to cool to room temperature, diisopropyl ether (53 mL) was added dropwise thereto at the same temperature, and the mixture was stirred to give crystals. The obtained crystals were collected by filtration, and washed with a mixed solvent (20 mL) of diisopropyl ether/ethyl acetate (1:1, volume ratio) to give wet crystals. The obtained wet crystals were dried under reduced pressure at an outside temperature of 50° C. to give N-methyl-6-[(1-tosyl-1H-imidazol-4-yl)carbonyl]-2-naphthamide (6.5 g, 15.0 mmol). yield 79%.

후처리

  1. filtrationThe insoluble material was filtered off from the obtained reaction mixture at 60° C.
  2. washwashed with N,N-dimethylacetamide (33 mL)
  3. washThe filtrate and washing
  4. temperaturecooled to 40° C.
  5. additionwater (49 mL) was added dropwise
  6. stirringthe mixture was stirred at the same temperature for 0.5 hr or more
  7. customat room temperature for 1 hr or more to give crystals
  8. filtrationThe obtained crystals were collected by filtration
  9. washwashed with water (51 mL)
  10. customto give wet crystals
  11. customThe obtained wet crystals were dried under reduced pressure at an outside temperature of 50° C.
  12. customto give crude crystals (6.6 g)
  13. temperatureThe obtained mixture was warmed to 50° C.
  14. stirringstirred for 0.5 hr or more
  15. custom13 mL of the solvent was evaporated under reduced pressure
  16. temperatureto cool to room temperature
  17. additiondiisopropyl ether (53 mL) was added dropwise
  18. stirringat the same temperature, and the mixture was stirred
  19. customto give crystals
  20. filtrationThe obtained crystals were collected by filtration
  21. washwashed with a mixed solvent (20 mL) of diisopropyl ether/ethyl acetate (1:1, volume ratio)
  22. customto give wet crystals
  23. customThe obtained wet crystals were dried under reduced pressure at an outside temperature of 50° C.

출처 및 근거

ORD 기록
ord-22ee88f860dc4010bf41bda54485c0a9
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278938B2

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