CHEMBRDG-BB 4024704 synthesis

5synthesis methods

Product Name:CHEMBRDG-BB 4024704
CAS Number:95262-01-4
Molecular formula:C10H11NO3
Molecular Weight:193.2

106-49-0
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$5.00/5G

105-53-3
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$5.00/25g

95262-01-4
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$44.00/250mg

Yield:95262-01-4 3.1 g

Reaction Conditions:

Stage #1: p-toluidine;diethyl malonate at 150; for 6 h;
Stage #2: with lithium hydroxide in tetrahydrofuran at 20; for 3 h;

Steps:

7.XXX.YYY; 7.XXX.ZZZ

YYY. Intermediate 40 Starting material (9.08 g, 84.4 mmol) was added to 19.2 ml of diethyl malonate, the mixture was heated to 150° C. (oil bath temperature) for 6 h, evaporated, filtered and washed with ethyl acetate to give 3.7 g of white solid, it was intermediate 41 (check it by LC-MS), the filtrate was evaporated, the residue cooled to afford second batch solid, washed with a solution of Petroleum ether:Ethyl acetate equal to 5:1, check it by LC-MS, it was intermediate 40 (5.42 g). ZZZ. Intermediate 42 To a stirred solution of intermediate 40 (5.42 g, 24.5 mmol) in THF, 60 ml of 2N LiOH was added and the resulting mixture was stirred at room temperature for 3 h. The solvent was evaporated, the residue washed with ethyl acetate, filtered, and the cake was added to 10 ml of concentrated HC1 and stirred for 30 min, then the cake was filtered and dried to give 3.1 g of product (intermediate 42).

References:

WO2021/194954,2021,A1 Location in patent:Paragraph 00363; 00428-00429