Dimethylamine → Evt-201

HRID 651574Notes

Reaction equation

HRID 651574 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:20]=[C:19]([CH2:21]Cl)[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:25][NH:26][CH3:27]>O1CCOCC1>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:20]=[C:19]([CH2:21][N:26]([CH3:27])[CH3:25])[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 224621917-Chloro-3-(5-chloromethyl-[1,2,4]oxadiazol-3-yl)-5-methyl-4,5-dihydro-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 9885841Evt-201

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7.0 g 7-Chloro-3-(5-chloromethyl-[1,2,4]oxadiazol-3-yl)-5-methyl-4,5-dihydro-imidazo-[1,5-a][1,4]benzodiazepin-6-one were suspended under stirring and argon atmosphere in 70 ml 1,4-dioxane and 25.7 ml dimethylamine (33% in ethanol) were added over 60 minutes. The reaction mixture was stirred one more hour at r.t. and then the solvents were removed under reduced pressure at 35° C. The residue was partitioned between 50 ml dichloromethane and 20 ml deionized water. The phases were separated and the organic phase was washed twice with 20 ml deionized water. The aqueous phases were extracted separately with the same portion of 25 ml dichloromethane, twice. The combined organic extracts were dried (Na2SO4) and the solvent was removed under reduced pressure. Crude product: 8.0 g as a light yellow foam.

Workup

  1. stirringThe reaction mixture was stirred one more hour at r.t.
  2. customthe solvents were removed under reduced pressure at 35° C
  3. customThe residue was partitioned between 50 ml dichloromethane and 20 ml
  4. customThe phases were separated
  5. washthe organic phase was washed twice with 20 ml
  6. extractionThe aqueous phases were extracted separately with the same portion of 25 ml dichloromethane
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e170966746f54cfe9be2b0fdaa7f4716
Source dataset
uspto-grants-2001_08
Patent number
US06281353B1

Reaction notes

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