HCID 15289396, compound → HCID 15289397, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][CH2:10][NH:11][C:12]([NH:14][NH:15]C(OC(C)(C)C)=O)=[O:13]>C(O)(C(F)(F)F)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][CH2:10][NH:11][C:12]([NH:14][NH2:15])=[O:13]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
In a first embodiment, a novel bifunctional compound was prepared by first reacting methoxycarbonylsulfenyl chloride with 2-aminoethanethiol hydrochloride, then 2-mercaptopyridine to form 2-[(2-pyridinyl)dithio]ethanamine hydrochloride (see FIG. 2). This compound was then reacted with phosgene in the presence of triethylamine (TEA), then t-butyl carbazate, to form N-[2-[(2-pyridinyl)dithio]ethyl]-2-(tert.-butoxy-carbonyl)hydrazinecarboxamide. The hydrazinecarboxamide was next dissolved in TFA to form N-[2-[(2-pyridinyl)dithio]ethyl]hydrazinecarboxamide, compound 10, a semicarbazide, which was then reacted with adriamycin hydrochloride to form the semicarbazone derivative of ADM containing a reactive pyridinyldithio moiety, compound 1, FIG. 1.
Sources & evidence
- ORD record
- ord-44d824e1c0a548fd81e80a37edebe565
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05137877
Reaction notes
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