Dimethylformamide → 3-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-7-chloro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1378044Notes

Reaction equation

HRID 1378044 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.[Cl:25][C:26]1[C:31]2[C:32](=[O:45])[N:33]([CH3:44])[CH2:34][C:35]3[N:36]([CH:37]=[N:38][C:39]=3[C:40](=[N:42][OH:43])[NH2:41])[C:30]=2[CH:29]=[CH:28][CH:27]=1.[CH3:46]N(C)C=O>>[C:1]([C:46]1[O:43][N:42]([CH2:13][NH2:15])[CH:40]([C:39]2[N:38]=[CH:37][N:36]3[C:30]4[CH:29]=[CH:28][CH:27]=[C:26]([Cl:25])[C:31]=4[C:32](=[O:45])[N:33]([CH3:44])[CH2:34][C:35]=23)[N:41]=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 541588047-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime

Product 1

HCID 677135773-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-7-chloro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-oneYield 96%

Procedure

2.45 g (14 mmol) of BOC-glycine were dissolved in 20 ml of N,N-dimethylformamide, whereupon the mixture was treated portionwise with 2.43 g (15 mmol) of 1,1'-carbonyldiimidazole and stirred at 50° for 20 min. After adding 3.8 g (12.4 mmol) of 7-chloro-5,6-dihydro-5-methyl-6-oxo-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 washed three times with water. After drying the solution, evaporation of the solvent and crystallization of the residue from ethyl acetate and hexane there were obtained 5.33 g (96%) of 3-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-7-chloro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of m.p. 144°-146°.

Workup

  1. stirringwas stirred at 90° overnight
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed three times with water
  5. customAfter drying
  6. customthe solution, evaporation of the solvent and crystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-f96b7f12d8824bdbb604f11449c8e8ca
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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