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US 12,006,291 B2Granted
Processes for the preparation of 4,6,7-trifluoro-1H-indole-2-carboxylic acid
AssigneeEnanta Pharmaceuticals, Inc.
InventorsKaicheng Zhu, Tao Wang, Jiajun Zhang, Hui Cao, Ruichao Shen, Guoqiang Wang, George G. Wu, Yat Sun Or
Life of this patent
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Abstract
The present invention relates to processes for preparing a Compound (1): or a pharmaceutically acceptable salt or solvate thereof. Compound (1) is useful as in many pharmaceutical agents, especially is useful as key intermediate in the synthesis of certain SARS-CoV-2 3CLpro inhibitors.
Claims7
A process for producing Compound (1),
- said process comprising the steps of:
- (i) reacting Compound (a) with a bromination agent, to produce Compound (b):
- (ii) reacting Compound (b) with N,O-dimethylhydroxylamine HCl, in the presence of an acid activation agent to produce Compound (c):
- (iii) reducing Compound (c) with a reducing reagent to produce Compound (d):
- (iv) reacting Compound (d) with Compound (d-1)
- to produce Compound (e):
- (v) reacting Compound (e) with a hydrogen source, to produce Compound (f):
- and
- (vi) hydrolyzing Compound (f) to produce Compound (1):
6 more elements
A process for producing the Compound (1),
- said process comprising the steps of:
- (1) reacting Compound (a) with a bromination agent, to produce Compound (b):
- (2) reacting Compound (b) with an acid activation reagent and a reducing agent to produce Compound (c-1):
- (3) reacting Compound (c-1) with oxidizing agent to produce Compound (d):
- (4) reacting Compound (d) with the compound of Formula (D-2)
- to yield the compound of Formula (E):
- wherein G6 is -Cbz, -Fmoc, -Moz, or -Pnz;
- (5) hydrolyzing the compound of Formula (E) to produce Compound (g):
- and
- (6) reacting Compound (g) with a hydrogen source in the presence of a hydrogenation catalyst, to produce Compound (1):
7 more elements
Dependencies are inferred from the claim text.