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US 9,751,863 B2Granted
Therapeutically active compounds and their methods of use
AssigneeAgios Pharmaceuticals, Inc.
InventorShijie Zhang
Life of this patent
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Abstract
Provided are compounds useful for treating cancer and methods of making the compounds and intermediates described herein.
Claims17
A method of preparing a compound having the formula (I):
- wherein ring A is pyridinyl substituted with trifluoromethyl, comprising reacting a compound of formula (II):
- wherein R is alkyl, alkenyl or alkynyl;
- with
- (biuret) in the presence of a dehydrating agent, wherein the dehydrating agent comprises (i) trimethyl orthoformate and a catalytic amount of trifluoroacetic acid or (ii) titanium(IV) ethoxide.
1 more element
A method of preparing a compound of formula (Ia):
- comprising reacting a compound of formula (IIa):
- with
- with (biuret) in the presence of a dehydrating reagent to provide the compound of formula (Ia), wherein the dehydrating agent comprises (i) trimethyl orthoformate and a catalytic amount of trifluoroacetic acid or (ii) titanium(IV) ethoxide.
A method of preparing a compound of formula (VIIIa)
- comprising a) reacting compound (Ia)
- with benzyltriethylammonium chloride and POCl3 to obtain compound (IVb)
- b) reacting compound (IVb) with 2-(trifluoromethyl)pyridin-4-amine to obtain compound (VIb)
- and
- c) reacting compound (VIb) with 1-amino-2-methylpropan-2-ol to obtain the compound of formula (VIIIa), wherein compound (Ia) is prepared by reacting
- with
- in the presence of a dehydrating reagent, wherein the dehydrating agent comprises (i) trimethyl orthoformate and a catalytic amount of trifluoroacetic acid or (ii) titanium(IV) ethoxide.
4 more elements
Dependencies are inferred from the claim text.