Methods and systems for synthesis of a D-aminoluciferin precursor and related compounds
Methods and systems to generate 6-amino-6-deoxy- D -luciferin precursor, 2-cyano-6-aminobenzothiazole and related compounds and derivatives.
1. A method to provide 2-cyano-6-aminobenzothiazole from a monofunctional benzothiazole, the method comprising:
providing the monofunctional benzothiazole ethyl benzothiazole-2-carboxylate and introducing a nitro group to position C6 of the ethyl benzothiazole-2-carboxylate;
attaching in position C2 a functional group of formula (I) (C(═X 1 )NH2) wherein X 1 is O; and
converting the functional group of formula (I) to a cyanide group through dehydration of the C(═O)NH2 group;
and reducing the nitro group in C6 to provide 2-cyano-6-aminobenzothiazole.
2. A method to provide 2-cyano-6-aminobenzothiazole from a monofunctional benzothiazole, the method comprising
providing a monofunctional benzothiazole selected from the group consisting of ethyl-6-nitrobenzothiazole-2-carboxylate and a ethyl benzothiazole-2-carboxylate;
converting the C2 functional group into an amide of formula (I) (C(═X 1 )NH 2 ) wherein X 1 is O; and
converting the amide of formula (I) to a cyanide group, through elimination of a H 2 X 1 compound,
wherein the monofunctional benzothiazole either comprises an amino group in position C6 or is modified to comprise an amino group in position C6.
3. The method of claim 2 wherein the converting of the C2 functional group into an amide of formula (I) is performed by reacting the monofunctional benzothiazole with an amine.
4. The method of claim 3 , wherein converting the amide of formula (I) to a cyanide group, is performed by dehydration of the C(═O)NH2 group.