2-Quinolinecarboxylicacid,6-amino-1,4-dihydro-4-oxo-(9CI) synthesis
- Product Name:2-Quinolinecarboxylicacid,6-amino-1,4-dihydro-4-oxo-(9CI)
- CAS Number:52980-10-6
- Molecular formula:C10H8N2O3
- Molecular Weight:204.18
52979-42-7
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52980-10-6
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Yield:-
Reaction Conditions:
Stage #1: 6-amino-4-hydroxy-2-methoxycarbonylquinolinewith lithium hydroxide monohydrate;water in methanol;
Stage #2: with hydrogenchloride in methanol;water; pH=7;
Steps:
Synthesis of Compound 27: 4-hydroxy-6-(6-(6-(5-((3aS,4S,6aR)-2-oxohexahydro-l H- thieno[3,4-d]imidazol-4-yl)pentanamido)hexanamido)hexanamido)quinoline-2- carboxylic aci
[0237] A mixture of compound 25 (327mg, 1.5 mmol) and LiOH.H20 (430 mg, 10 mmol) were stirred in MeOH (10 ml) overnight, then carefully acidified 6N HC1 to pH 7, concentrated to remove MeOH. The crude was then diluted with acetonitriie and water (lOml/lOml), and NaHC03 (1 ,26g) was added, followed by addition of Biotin-LC-LC-NHS (852mg, 1.5 mmol). The mixture was stirred vigorously for 1 day, acidified by 6N HC1, the resulting solids were filtered, and washed with MeOH, followed by water, then dried to produce the pure compound 27 (140mg). MS: 657.2(M+H)+, 4-hydroxy-6-(6-(6-(5- ((3aS,4S,6aR)-2-oxohexahydro-lH-thieno[3,4-d]imidazol-4- yl)pentanamido)hexanamido)hexanamido)quinoline-2-carboxylic acid.
References:
WO2014/188377,2014,A2 Location in patent:Paragraph 0237
859982-04-0
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52980-10-6
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24782-43-2
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52980-10-6
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