Process for preparation of isoxazoline substituted benzamide compound
AssigneeCadila Healthcare Limited
InventorsKumar Kamlesh SINGH, Sanjay Jagdish DESAI, Kuldeep Natwarlal JAIN, Jitesh Amratlal DESAI, Sarvil Dhirajbhai PATEL
Life of this patent
Estimating the term…
Abstract
The invention relates to process for the preparation of isoxazoline-substituted benzamide compound and intermediates thereof. The invention also relates to process for the preparation of Fluralaner and intermediates thereof.
Claims18
A process for the preparation of fluralaner, the process comprising:
- (a) reacting a compound of Formula (VI) with a compound of Formula (VII),
- to obtain a compound of Formula (V),
- wherein M is Cs;
- (b) converting the compound of Formula (V) into a compound of Formula (IV) or its reactive derivative;
- (c) reacting the compound of Formula (IV) or its reactive derivative with 2-Amino-N-(2,2,2-trifluoroethyl)acetamide, or salts thereof to obtain a compound of Formula (II);
- and
- (d) reacting the compound of Formula (II) with hydroxylamine, or salts thereof to obtain fluralaner.
A process for preparation of fluralaner, the process comprising:
- (c) reacting a compound of Formula (IV) or its reactive derivative with 2-Amino-N-(2,2,2-trifluoroethyl)acetamide or salts thereof to obtain a compound of Formula (II);
- and
- (d) reacting the compound of Formula (II) with hydroxylamine or salts thereof to obtain fluralaner.
The process according to claim 10, wherein the reaction at step (a) is performed in the presence of a base selected from sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, sodium bicarbonate, triethylamine, pyridine, 4-(dimethylamino)pyridine, DBU, DBN N, N-dimethylaniline, imidazole, and tributylamine
A compound of Formula (V),
- wherein M is Cs.
A process for the preparation of fluralaner, comprising reacting a compound of Formula (X) with 2-Amino-N-(2,2,2-trifluoroethyl)acetamide or salts thereof to obtain fluralaner,
- wherein B is sodium, potassium, cesium, methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, t-butylamine, n-pentylamine, isopentylamine, benzylamine, aniline, dimethlamine, diethylamine, dipropylamine, di-isopropylamine, dibutylamine, diisobutylamine, dipentylamine, diisopentylamine, pyrrolidine, piperidine, piperazine, morpholine, dibenzylamine, tributylamine, tripentylamine, trimethylamine, tripropylamine, tribenzylamine, diisopropylethylamine, or N-methylmorpholine.
A compound of Formula (X),
- wherein B is sodium, potassium, cesium, methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, t-butylamine, n-pentylamine, isopentylamine, benzylamine, aniline, dimethlamine, diethylamine, dipropylamine, di-isopropylamine, dibutylamine, diisobutylamine, dipentylamine, diisopentylamine, pyrrolidine, piperidine, piperazine, morpholine, dibenzylamine, tributylamine, tripentylamine, trimethylamine, tripropylamine, tribenzylamine, diisopropylethylamine, or N-methylmorpholine.
A process for the preparation of compound of Formula (X), comprising reacting 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-2-enoyl)-2-methylbenzoic acid with hydroxyl amine or its salts.
Dependencies are inferred from the claim text.