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CAS 104-94-9

1-Amino-4-methoxybenzene4-Methoxyphenylamine4-methoxyaniline

Codes: (II)101438-4-a, (II)101438-13-a, (II)101438-70-a, Imipenem-015, (II)140605-24-a, POSA-041

Application context (from source-drug indications)

Breast cancerPaclitaxel/Encequidar mesylateAdenocarcinomaPaclitaxel/Encequidar mesylateAngiosarcomaPaclitaxel/Encequidar mesylateSolid tumourPaclitaxel/Encequidar mesylateBacterial pneumoniaCilastatin Sodium/Imipenem/RelebactamHospital-acquired pneumoniaCilastatin Sodium/Imipenem/RelebactamInfectious diseaseCilastatin Sodium/Imipenem/RelebactamBacteraemiaCilastatin Sodium/Imipenem/RelebactamVentilator-associated pneumoniaCilastatin Sodium/Imipenem/RelebactamHealthcare-associated pneumoniaCilastatin Sodium/Imipenem/RelebactamBladder cancerDocetaxel polymeric micelle (Samyang Biopharmaceuticals)Head and neck cancerDocetaxel polymeric micelle (Samyang Biopharmaceuticals)Head and neck squamous cell carcinomaDocetaxel polymeric micelle (Samyang Biopharmaceuticals)Solid tumourDocetaxel polymeric micelle (Samyang Biopharmaceuticals)CandidiasisPosaconazoleAspergillus infectionPosaconazoleFungal infectionPosaconazoleOral candidiasisPosaconazoleCoccidioidomycosisPosaconazoleHistoplasmosisPosaconazolePancreatic cancerPaclitaxelNon-small cell lung cancerPaclitaxelHodgkin's diseasePaclitaxelSeminomaPaclitaxelOvarian cancerPaclitaxelBreast cancerPaclitaxelBacterial infectionImipenemGonorrhoeaImipenemBacillus anthracis infectionImipenemNon-small cell lung cancerDocetaxel (Beihai)Prostate cancerDocetaxel (Beihai)Castration-resistant prostate cancerDocetaxel (Beihai)Breast cancerDocetaxel (Beihai)Head and neck cancerDocetaxel (Beihai)Head and neck squamous cell carcinomaDocetaxel (Beihai)

Source drugs (routes using this intermediate)

DrugTierExpiry
Paclitaxel/Encequidar mesylateTier C — Watch / trade-
Cilastatin Sodium/Imipenem/RelebactamTier C — Watch / trade-
Docetaxel polymeric micelle (Samyang Biopharmaceuticals)Tier C — Watch / trade-
PosaconazoleTier C — Watch / trade-
PaclitaxelTier B — Position early-
ImipenemTier C — Watch / trade-
Docetaxel (Beihai)Tier C — Watch / trade-

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.

Paclitaxel/Encequidar mesylateOptimised routesteps: 9total yield: /
(3-Bromophenyl)formaldehyde→1-Amino-4-methoxybenzene→(NZ)-N-[(3-bromophenyl)methylidene]-4-methoxyaniline→(2-Chloranyl-2-oxidanylideneethyl) ethanoate→alpha-Chlorobenzaldehyde→(2S,3R)-2-(3-bromophenyl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl acetate→(2S,3R)-2-(3-bromophenyl)-4-oxoazetidin-3-yl acetate→(3R,4S)-4-(3-bromophenyl)-3-hydroxyazetidin-2-one→(3R,4S)-4-(3-bromophenyl)-3-[(triethylsilyl)oxy]azetidin-2-one→(3R,4S)-1-benzoyl-4-(3-bromophenyl)-3-[(triethylsilyl)oxy]azetidin-2-one→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1,7,13-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-(3-bromophenyl)-3-(phenylformamido)-2-[(triethylsilyl)oxy]propanoyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-(3-bromophenyl)-2-hydroxy-3-(phenylformamido)propanoyl]oxy}-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-13-[[(2R,3S)-3-benzamido-2-hydroxy-3-(3-tritiophenylpropanoyl]oxy]-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
Cilastatin Sodium/Imipenem/RelebactamOptimised routesteps: 9total yield: /
4-Methoxyphenylamine→1-Amino-4-fluorobenzene→4-Bromophenylamine→4-Ethoxyphenylamine→omega-Bromoacetophenone→Chloroacetyl chloride→2-Iodo-1-(3-methoxyphenyl)ethanone→1-Bromo-3,3-dimethylbutan-2-one<-fgf->→2-[(4-Methoxyphenyl)amino]-1-phenylethanone→1-[(4-Methoxyphenyl)amino]acetone→1-[(4-Fluorophenyl)amino]acetone→2-[(4-Bromophenyl)amino]-1-(3-methoxyphenyl)ethanone→1-[(4-Ethoxyphenyl)amino]-3,3-dimethylbutan-2-one→(3S)-4-Benzoyl-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-1-(4-fluorophenyl)azetidin-2-one→(3S)-1-(4-Bromophenyl)-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-4-(3-methoxybenzoyl)azetidin-2-one→(3S)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-4-(2,2-dimethylpropanoyl)-1-(4-ethoxyphenyl)azetidin-2-one→(2R,3R)-3-Methyloxirane-2-carboxylic acid→L-Threonine→(2R,3R)-N-(4-Methoxyphenyl)-3-methyl-N-(2-oxo-2-phenylethyl)oxirane-2-carboxamide→(2R,3R)-N-(4-Methoxyphenyl)-3-methyl-N-(2-oxopropyl)oxirane-2-carboxamide→(2R,3R)-N-(4-Fluorophenyl)-3-methyl-N-(2-oxopropyl)oxirane-2-carboxamide→(2R,3R)-N-(4-Bromophenyl)-N-[2-(3-methoxyphenyl)-2-oxoethyl]-3-methyloxirane-2-carboxamide→(2R,3R)-N-(3,3-Dimethyl-2-oxobutyl)-N-(4-ethoxyphenyl)-3-methyloxirane-2-carboxamide→(3S)-4-Benzoyl-3-[(1R)-1-hydroxyethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-3-[(1R)-1-hydroxyethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-1-(4-fluorophenyl)-3-[(1R)-1-hydroxyethyl]azetidin-2-one→(3S)-1-(4-Bromophenyl)-3-[(1R)-1-hydroxyethyl]-4-(3-methoxybenzoyl)azetidin-2-one→(3S)-4-(2,2-Dimethylpropanoyl)-1-(4-ethoxyphenyl)-3-[(1R)-1-hydroxyethyl]azetidin-2-one→(1E)-1-[(4-Methoxyphenyl)imino]acetone→S-Pyridin-2-yl (3R)-3-[[tert-butyl(dimethyl)silyl]oxy]butanethioate→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl acetate→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl acetate→(2R,3R)-1-(4-Bromophenyl)-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-4-oxoazetidin-2-yl acetate→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-ethoxyphenyl)-4-oxoazetidin-2-yl acetate→(2S,3S)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylic acid→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-4-oxoazetidin-2-yl acetate
PaclitaxelOptimised routesteps: 9total yield: /
(3-Bromophenyl)formaldehyde→1-Amino-4-methoxybenzene→(NZ)-N-[(3-bromophenyl)methylidene]-4-methoxyaniline→(2-Chloranyl-2-oxidanylideneethyl) ethanoate→alpha-Chlorobenzaldehyde→(2S,3R)-2-(3-bromophenyl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl acetate→(2S,3R)-2-(3-bromophenyl)-4-oxoazetidin-3-yl acetate→(3R,4S)-4-(3-bromophenyl)-3-hydroxyazetidin-2-one→(3R,4S)-4-(3-bromophenyl)-3-[(triethylsilyl)oxy]azetidin-2-one→(3R,4S)-1-benzoyl-4-(3-bromophenyl)-3-[(triethylsilyl)oxy]azetidin-2-one→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-1,7,13-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-(3-bromophenyl)-3-(phenylformamido)-2-[(triethylsilyl)oxy]propanoyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-(3-bromophenyl)-2-hydroxy-3-(phenylformamido)propanoyl]oxy}-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate→(2alpha,5beta,7beta,10beta,13alpha)-4,10-Bis(acetyloxy)-13-[[(2R,3S)-3-benzamido-2-hydroxy-3-(3-tritiophenylpropanoyl]oxy]-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
ImipenemOptimised routesteps: 9total yield: /
4-Methoxyphenylamine→1-Amino-4-fluorobenzene→4-Bromophenylamine→4-Ethoxyphenylamine→omega-Bromoacetophenone→Chloroacetyl chloride→2-Iodo-1-(3-methoxyphenyl)ethanone→1-Bromo-3,3-dimethylbutan-2-one<-fgf->→2-[(4-Methoxyphenyl)amino]-1-phenylethanone→1-[(4-Methoxyphenyl)amino]acetone→1-[(4-Fluorophenyl)amino]acetone→2-[(4-Bromophenyl)amino]-1-(3-methoxyphenyl)ethanone→1-[(4-Ethoxyphenyl)amino]-3,3-dimethylbutan-2-one→(3S)-4-Benzoyl-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-1-(4-fluorophenyl)azetidin-2-one→(3S)-1-(4-Bromophenyl)-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-4-(3-methoxybenzoyl)azetidin-2-one→(3S)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-4-(2,2-dimethylpropanoyl)-1-(4-ethoxyphenyl)azetidin-2-one→(2R,3R)-3-Methyloxirane-2-carboxylic acid→L-Threonine→(2R,3R)-N-(4-Methoxyphenyl)-3-methyl-N-(2-oxo-2-phenylethyl)oxirane-2-carboxamide→(2R,3R)-N-(4-Methoxyphenyl)-3-methyl-N-(2-oxopropyl)oxirane-2-carboxamide→(2R,3R)-N-(4-Fluorophenyl)-3-methyl-N-(2-oxopropyl)oxirane-2-carboxamide→(2R,3R)-N-(4-Bromophenyl)-N-[2-(3-methoxyphenyl)-2-oxoethyl]-3-methyloxirane-2-carboxamide→(2R,3R)-N-(3,3-Dimethyl-2-oxobutyl)-N-(4-ethoxyphenyl)-3-methyloxirane-2-carboxamide→(3S)-4-Benzoyl-3-[(1R)-1-hydroxyethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-3-[(1R)-1-hydroxyethyl]-1-(4-methoxyphenyl)azetidin-2-one→(3S)-4-Acetyl-1-(4-fluorophenyl)-3-[(1R)-1-hydroxyethyl]azetidin-2-one→(3S)-1-(4-Bromophenyl)-3-[(1R)-1-hydroxyethyl]-4-(3-methoxybenzoyl)azetidin-2-one→(3S)-4-(2,2-Dimethylpropanoyl)-1-(4-ethoxyphenyl)-3-[(1R)-1-hydroxyethyl]azetidin-2-one→(1E)-1-[(4-Methoxyphenyl)imino]acetone→S-Pyridin-2-yl (3R)-3-[[tert-butyl(dimethyl)silyl]oxy]butanethioate→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl acetate→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl acetate→(2R,3R)-1-(4-Bromophenyl)-3-[(1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-4-oxoazetidin-2-yl acetate→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-ethoxyphenyl)-4-oxoazetidin-2-yl acetate→(2S,3S)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylic acid→(2R,3R)-3-[(1R)-1-[[tert-Butyl(dimethyl)silyl]oxy]ethyl]-4-oxoazetidin-2-yl acetate

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