Dimethylformamide → HCID 70075035, compound

HRID 1378127Notes

Reaction equation

HRID 1378127 reaction equation
[C:1](N1C=CN=C1)([N:3]1C=CN=C1)=O.[C:13](NCC(O)=O)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[NH2:25]/[C:26](=[N:42]\[OH:43])/[C:27]1[N:28]=[CH:29][N:30]2[C:36]3[S:37][CH:38]=[CH:39][C:35]=3[C:34](=[O:40])[N:33]([CH3:41])[CH2:32][C:31]=12.[CH3:44]N(C)C=O>>[C:13]([C:44]1[O:43][N:42]([CH2:1][NH2:3])[CH:26]([C:27]2[N:28]=[CH:29][N:30]3[C:36]4[S:37][CH:38]=[CH:39][C:35]=4[C:34](=[O:40])[N:33]([CH3:41])[CH2:32][C:31]=23)[N:25]=1)([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 22914469HCID 22914469, compound

Product 1

HCID 70075035HCID 70075035, compoundYield 73%

Procedure

5.40 g (33.3 mmol) of 1,1'-carbonyldiimidazole were added to a solution of 5.40 g (30.5 mmol) of BOC-glycine in 150 ml of N,N-dimethylformamide and the mixture was stirred at 50° for 30 minutes. Subsequently, 7.70 g (7.58 mmol) of (E)- and/or (Z)-7-(amino-hydroxyiminomethyl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[3,2-f][1,4]diazepin-4-one were added and the mixture was stirred at 90° for 15 hours. The brown solution obtained was evaporated in a high vacuum and the brown residue obtained was chromatographed (silica gel, methylene chloride/methanol 19:1). There were obtained 8.40 g (73%) of 7-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[3,2-f][1,4]diazepin-4-one as a colourless foam, Rf=0.35 (silica gel, methylene chloride/methanol 19:1).

Workup

  1. stirringthe mixture was stirred at 90° for 15 hours
  2. customThe brown solution obtained
  3. customwas evaporated in a high vacuum
  4. customthe brown residue obtained
  5. customwas chromatographed (silica gel, methylene chloride/methanol 19:1)

Sources & evidence

ORD record
ord-5f7a5ea5ebbc4bdd95be9beb3d59ab03
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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