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CAS 923289-21-8
2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol
Codes: SIME-007
Application context (from source-drug indications)
Hepatitis CSimeprevir SodiumChronic hepatitis CSimeprevir SodiumMeaslesSimeprevir SodiumMycobacterium tuberculosis infectionSimeprevir Sodium
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Simeprevir Sodium | Tier B — Position early | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid→N-methylhex-5-en-1-amine→(1R,4R,5R)-N-(hex-5-en-1-yl)-N-methyl-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamide→(1R,2R,4R)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-hydroxycyclopentanecarboxylic acid→(1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate hydrochloride→(1R,2S)-ethyl 1-((1R,2R,4S)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-hydroxycyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate→2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol→(1R,2S)-ethyl 1-((1R,2R,4R)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate→(2R,3aR,11aS,12aR,14aR,Z)-ethyl 2-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)-5-methyl-4,14-dioxo-1,2,3,3a,4,5,6,7,8,9,11a,12,12a,13,14,14a-hexadecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a-carboxylate→cyclopropanesulfonamide
N-methylhex-5-en-1-amine→2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol→(1R,2S)-ethyl 1-((1R,2R,4R)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate→tetraethyl butane-1,2,3,4-tetracarboxylate→4-oxocyclopentane-1,2-dicarboxylic acid→4-hydroxycyclopentane-1,2-dicarboxylic acid→4-hydroxycyclopentane-1,2-dicarboxylic acid→ethyl carbonochloridate→3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid→(1S,4R,5R)-benzyl 3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylate→butane-1,2,3,4-tetracarboxylic acid→(1R,2R,4R)-1-benzyl 2-methyl 4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentane-1,2-dicarboxylate→(1R,2R,4S)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)-2-(methoxycarbonyl)cyclopentanecarboxylic acid→(1R,2R,4S)-methyl 2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxylate→lithium (1R,2R,4S)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxylate→(1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate
N-methylhex-5-en-1-amine→(1R,4R,5R)-N-(hex-5-en-1-yl)-N-methyl-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamide→2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol→4-hydroxycyclopentane-1,2-dicarboxylic acid→(1R,2R,4S)-methyl 2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxylate→(1R)-quinolin-4-yl((1S,4S,5R)-5-vinylquinuclidin-2-yl)methanol (1R,4R,5R)-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylate→(1R,2R,4R)-methyl 2-(hex-5-en-1-yl(methyl)carbamoyl)-4-hydroxycyclopentanecarboxylate
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