Dimethylformamide → 3-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1378134Notes

Reaction equation

HRID 1378134 reaction equation
[C:1](NCC(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:13](N1C=CN=C1)([N:15]1C=CN=C1)=O.[CH3:25][N:26]1[C:32](=[O:33])[C:31]2[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=2[N:29]2[CH:38]=[N:39][C:40]([C:41](=[N:43][OH:44])[NH2:42])=[C:28]2[CH2:27]1.[CH3:45]N(C)C=O>>[C:1]([C:45]1[O:44][N:43]([CH2:13][NH2:15])[CH:41]([C:40]2[N:39]=[CH:38][N:29]3[C:30]4[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=4[C:32](=[O:33])[N:26]([CH3:25])[CH2:27][C:28]=23)[N:42]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 566103035,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime

Product 1

HCID 700739213-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-oneYield 87%

Procedure

10.5 g (60 mmol) of BOC-glycine were dissolved in 50 ml of N,N-dimethylformamide, treated portionwise with 9.73 g (60 mmol) of 1,1'-carbonyldiimidazole and stirred at 55° for 20 minutes. After adding 15.5 g (57.1 mmol) of 5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime the mixture was stirred at 90° overnight. The reaction mixture was concentrated, the residue was dissolved in methylene chloride and the solution was washed three times with water. After drying the solution, evaporating the solvent and crystallizing the residue from ethanol there were obtained 20.4 g (87%) of 3-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of m.p. 108°-113°.

Workup

  1. stirringwas stirred at 90° overnight
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washthe solution was washed three times with water
  5. customAfter drying the solution
  6. customevaporating the solvent
  7. customcrystallizing the residue from ethanol

Sources & evidence

ORD record
ord-7454407e396245f59b23a4f686b4274f
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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