Dimethylformamide → HCID 70076426, compound
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[CH:37]=[CH:38][S: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[CH:37]=[CH:38][S: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
Procedure
3.82 g (23.5 mmol) of 1,1'-carbonyldiimidazole were added to a solution of 3.85 g (21.9 mmol) of BOC-glycine in 45 ml of dimethylformamide and the mixture was stirred at 50° for 30 minutes. Subsequently, 5.7 g (20.56 mmol) of (E)- and/or (Z)-3-(aminohydroxyimino-methyl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-6-one were added thereto 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 10:1). There were obtained 7.2 g (84%) of not quite pure 3-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-6-one as a colourless foam, Rf=0.28 (silica gel, methylene chloride/methanol 10:1).
Workup
- stirringthe mixture was stirred at 90° for 15 hours
- customThe brown solution obtained
- customwas evaporated in a high vacuum
- customthe brown residue obtained
- customwas chromatographed (silica gel, methylene chloride/methanol 10:1)
Sources & evidence
- ORD record
- ord-3710967cb2b84d4eb413043685ade984
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05665718
Reaction notes
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