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US 10,519,185 B2Granted
Methods of preparing substituted nucleoside analogs
AssigneeAlios BioPharma, Inc.
InventorsVladimir Serebryany, Jyanwei Liu, Leonid Beigelman
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Abstract
Disclosed herein are methods of preparing a nucleoside analog, Compound (I): or a pharmaceutically acceptable salt thereof, which is useful in treating diseases and/or conditions such as viral infections, and intermediates thereof.
Claims51
A method of preparing a compound of formula (I):
- or a pharmaceutically acceptable salt thereof, comprising:
- forming a sulfonate at the 4-position of the uracil base of a compound of formula (KK);
- and converting the sulfonate to the compound of formula (I), or a pharmaceutically acceptable salt thereof, via aminolysis;
- wherein the compound of formula (KK) is:
1 more element
A method of preparing a compound of formula (I):
- or a pharmaceutically acceptable salt thereof, comprising:
- a) triflating a compound of formula (EE):
- wherein R3 is a trisubstituted silyl group, to provide a compound of formula (FF):
- wherein:
- R1 is trifluoromethanesulfonyl (Tf);
- R2 is trifluoromethanesulfonyl (Tf);
- and
- R3 is the trisubstituted silyl group of formula (EE);
- b) contacting the compound of formula (FF) with a base to provide a compound of formula (GG):
- wherein:
- R2 the trifluoromethanesulfonyl group of formula (FF);
- and
- R3 is the trisubstituted silyl group of formula (FF);
- c) chlorinating the compound of formula (GG) with a chloride source to provide a compound of formula (HH):
- wherein R3 is the trisubstituted silyl group of formula (GG);
- d) hydrolyzing the compound of formula (HH) to provide a compound of formula (II):
- wherein R3 is the trisubstituted silyl group of formula (HH);
- e) contacting the compound of formula (II) with a fluoride source to provide a compound of formula (JJ):
- f) esterifying the compound of formula (JJ) to provide a compound of formula (KK):
- and
- g) forming a sulfonate at the 4-position of the uracil base of the compound of formula (KK);
- and converting the sulfonate to the compound of formula (I), or a pharmaceutically acceptable salt thereof, via aminolysis.
19 more elements
Dependencies are inferred from the claim text.