Hydrazine → HCID 86746053, compound
Reaction equation
NN.CO[C:5]([S:7][Cl:8])=O.[SH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1>>[ClH:8].[NH2:11][CH2:10][CH:15]=[CH:14][CH2:5][S:7][S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1Participants
Procedure
In yet another preferred embodiment, a novel thiosemicarbazide bifunctional compound was formed (FIG. 4). In this embodiment, potassium phthalimide was reacted with 1,4-dibromo-2-butene to form 1-bromo-4-(N-phtalimido)-2butene. This compound was reacted with potassium thioacetate to form 1-(acetylthio)-4-(N-phthalimido)-2-butene which was then reacted with hydrazine and was treated with methoxycarbonylsulfenyl chloride followed by 2-mercaptopyridine to form 1-amino-4-[(2-pyridinyl)dithio]-2-butene hydrochloride. This compound was combined with TEA followed by di-2-pyridyl thionocarbonate, then t-butyl carbazate was added to form the t-boc derivative of N-[4-[(2-pyridinyl)dithio]-2-butenyl]-hydrazinecarbothioamide, compound 12. This compound was dissolved in TFA to form a compound in the form of a gum, which was then reacted with adriamycin hydrochloride and TFA to form the thiosemicarbazone derivative of ADM having a thiosemicarbazone bond at the C-13 position of the ADM (compound 3, FIG. 1) and having a reactive pyridinyldithio moiety.
Sources & evidence
- ORD record
- ord-5f1db155c6374888977acef55a5a28fa
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05349066
Reaction notes
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