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

HRID 922716Notes

Reaction equation

HRID 922716 reaction equation
[OH:1][CH:2]([C:17]1[N:18]=[CH:19][N:20]([C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[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]([C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH:21]=3)=[O:1])[CH:4]=2)[CH:9]=1)=[O:14]

Participants

5

Reactant 2

HCID 31374DimethylacetamideHCID 574658056-(hydroxy(1-trityl-1H-imidazol-4-yl)methyl)-N-methyl-2-naphthamide

Product 1

HCID 18769037N-methyl-6-((trityl-1H-imidazol-4-yl)carbonyl)-2-naphthamideYield 89.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

6-[Hydroxy(1-trityl-1H-imidazol-4-yl)methyl]-N-methyl-2-naphthamide (10.0 g, 19.1 mmol) and manganese dioxide (6.6 g, 75.9 mmol) were added to N,N-dimethylacetamide (85 mL), and the mixture was stirred at 60° C. for 2 hr. The insoluble material was filtered off at the same temperature, and washed with N,N-dimethylacetamide (40 mL). The filtrate and washing were combined and cooled to 40° C., water (60 mL) was added dropwise thereto, and the mixture was stirred at room temperature. The obtained crystals were collected by filtration, and washed with water (50 mL). The wet crystals were dried under reduced pressure to give crude crystals (9.5 g). Ethyl acetate (100 mL) was warmed to 40° C., and the crude crystals (9.5 g) were added thereto. The obtained mixture was warmed to 50° C., and stirred for 0.5 hr. The solvent (20 mL) was evaporated under reduced pressure. The residue was allowed to cool to room temperature, and diisopropyl ether (80 mL) was added dropwise thereto, and the mixture was stirred at the same temperature. The obtained crystals were collected by filtration, and washed with a mixed solvent (30 mL) of diisopropyl ether/ethyl acetate (1:1, volume ratio). The obtained wet crystals were dried under reduced pressure to give N-methyl-6-[(1-trityl-1H-imidazol-4-yl)carbonyl]-2-naphthamide (8.9 g, 17.1 mmol). yield 89%.

Workup

  1. filtrationThe insoluble material was filtered off at the same temperature
  2. washwashed with N,N-dimethylacetamide (40 mL)
  3. washThe filtrate and washing
  4. temperaturecooled to 40° C.
  5. additionwater (60 mL) was added dropwise
  6. stirringthe mixture was stirred at room temperature
  7. filtrationThe obtained crystals were collected by filtration
  8. washwashed with water (50 mL)
  9. customThe wet crystals were dried under reduced pressure
  10. customto give crude crystals (9.5 g)
  11. temperatureThe obtained mixture was warmed to 50° C.
  12. stirringstirred for 0.5 hr
  13. customThe solvent (20 mL) was evaporated under reduced pressure
  14. temperatureto cool to room temperature
  15. additiondiisopropyl ether (80 mL) was added dropwise
  16. stirringthe mixture was stirred at the same temperature
  17. filtrationThe obtained crystals were collected by filtration
  18. washwashed with a mixed solvent (30 mL) of diisopropyl ether/ethyl acetate (1:1, volume ratio)
  19. customThe obtained wet crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-c4cffbdd7d8e447fb45e51e5974e5944
Source dataset
uspto-grants-2016_03
Patent number
US09278938B2

Reaction notes

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