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US 12,110,275 B2Granted
Methods of synthesizing 2-[4-[(2,3,4-trimethoxyphenyl)methyl] piperazin-1-yl]ethyl pyridine-3-carboxylate
AssigneeImbria Pharmaceuticals, Inc.
InventorsNeil Buckley, Dan Belmont, Bryan Hauser, Myoung Goo Kim, Kumar Kannan
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Abstract
The invention provides methods of chemical synthesis of the pharmacological agent 2-[4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl]ethyl pyridine-3-carboxylate, also called CV-8972. The methods entail formation of a free base form of 2-[4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl]ethanol, also called CV-8814, as intermediate without producing a salt form of CV-8814.
Claims14
A method for preparing a compound of Formula (X):
- the method comprising the steps of:
- reacting a compound of Formula (1):
- with a compound of Formula (2):
- with sodium triacetoxyborohydride, in the presence of acetic acid and 2-methyltetrahydrofuran to produce a free base form of a compound of Formula (IX):
- and
- reacting the free base form of a compound of Formula (IX) with a compound of Formula (3):
- in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide and 4-(dimethylamino)pyridine in dichloromethane to produce the compound of Formula (X).
4 more elements
Dependencies are inferred from the claim text.