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US 2017/0362262 A1Published application
A process for preparing halogenated azaindole compounds using pybrop
AssigneeViiV Healthcare UK (No.4) Limited
InventorsMichael S. BULTMAN, Benjamin COHEN, Francisco GONZALEZ-BOBES, Matthew R. HICKEY
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Abstract
A process for preparing halogenated azaindole compounds makes use of a brominating agent PyBroP, together with a dehydrating agent BSA to enhance the selectivity and improve the yield of the final product which is a piperazine prodrug useful as an antiviral.
Claims11
A process for preparing a compound of formula I,
- said process comprising the steps of:
- (a) performing an oxidation reaction on the compound
- to yield the compound
- (b) performing a halogenation reaction on the compound obtained in step (a) to obtain the compound
- and
- (c) performing a deprotection reaction on the compound obtained in step (b) to prepare the compound of formula I above;
- wherein X1 is selected from the group of H,
- and Y is Br.
5 more elements
A process for preparing a compound of formula II
- said process comprising the steps of:
- (a) performing an oxidation reaction on the compound
- using H2O2, phthalic anhydride and solvent to yield the compound
- and
- (b) performing a bromination reaction on the compound obtained in step (a) using PyBroP and BSA to obtain the compound
- and
- (c) performing a deprotection reaction on the compound obtained in step (b) using toluene together with solvent to prepare the compound of formula II or its salts thereof.
4 more elements
A method of making a compound of formula III
- said process comprising the steps of:
- (a) performing an oxidation reaction on the compound
- using H2O2, phthalic anhydride and dichloromethane to yield the compound
- and
- (b) performing a bromination reaction on the compound obtained in step (a) using PyBroP and BSA to obtain the compound
- (c) performing a deprotection reaction on the compound obtained in step (b) using toluene in conjunction with t-amyl alcohol, followed by crystallization, to obtain the compound
- (d) reacting the compound obtained in step (c) to obtain the compound
- followed by reacting it with compound
- in an activation reaction to produce the compound
- and
- (e) adding the triazolyl compound
- in the presence of Cu ion and a ligand to obtain the compound
- wherein said ligand is selected from the group of 1,2-diaminocyclohexane, trans-1,2-diaminocyclohexane, cis-/trans-diaminocyclohexane, cis-N,N′-dimethyl-1,2-diaminocyclohexane, trans-N,N′-dimethyl-1,2-diaminocyclohexane, cis-/trans-N,N′-dimethyl-1,2-diaminocyclohexane, 1,2-diaminoethane, N,N′-dimethyl-1,2-diaminoethane, 1,10-phenanthroline, 4,7-diphenyl-1,10-phenantroline, 5-methyl-1,10-phenanthroline, 5-chloro-1,10-phenantroline, and 5-nitro-1,10-phenanthroline;
- and
- (f) reacting the compound obtained in step (e) with (tert-BuO)2POOCH2Cl to produce the compound
- and reacting the compound obtained in step f with an acid to yield compound of formula III above.
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Dependencies are inferred from the claim text.