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CAS 108282-38-8

4-Amino-5-chloro-2-ethoxybenzoic acid

Codes: Mosapride Citrate-005

Application context (from source-drug indications)

GastritisMosapride CitrateEnteral feeding intoleranceMosapride CitrateIrritable bowel syndromeMosapride CitrateDyspepsiaMosapride CitrateConstipationMosapride Citrate

Source drugs (routes using this intermediate)

DrugTierExpiry
Mosapride CitrateTier 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.

Mosapride CitrateOptimised routesteps: 5total yield: /
Methyl 4-(acetylamino)-2-hydroxybenzoate→1-Iodoethane→methyl 4-acetamido-2-ethoxybenzoate→methyl 5-chloro-4-acetamido-2-ethoxybenzoate→4-Amino-5-chloro-2-ethoxybenzoic acid→[4-(4-Fluorobenzyl)-2-morpholinyl]methylamine→Mosapride Citrate-007
Mosapride CitrateOptimised routesteps: 10total yield: /
(4-Fluorophenyl)methanone→1-Amino-2-hydroxyethane→2-(4-Fluorobenzylamino)ethanol→(+/-)-2-(Chloromethyl)oxirane→1-chloro-3-{[(4-fluorophenyl)methyl](2-hydroxyethyl)amino}propan-2-ol→2-(chloromethyl)-4-[(4-fluorophenyl)methyl]morpholine→{4-[(4-fluorophenyl)methyl]morpholin-2-yl}methanol→{4-[(4-fluorophenyl)methyl]morpholin-2-yl}methyl 4-methylbenzene-1-sulfonate→[(2S)-4-[(4-fluorophenyl)methyl]morpholin-2-yl]methyl phenylmethanesulfonate→[(2R)-4-[(4-fluorophenyl)methyl]morpholin-2-yl]methyl phenylmethanesulfonate→[(2R)-4-[(4-fluorophenyl)methyl]morpholin-2-yl]methanamine→[(2S)-4-[(4-fluorophenyl)methyl]morpholin-2-yl]methanamine→4-Amino-5-chloro-2-ethoxybenzoic acid
Mosapride CitrateOptimised routesteps: 6total yield: /
2-(4-Fluorobenzylamino)ethanol→2-Chloro-2-propenonitrile→4-[(4-fluorophenyl)methyl]morpholine-2-carbonitrile→ethyl 4-[(4-fluorophenyl)methyl]morpholine-2-carboxylate→{4-[(4-fluorophenyl)methyl]morpholin-2-yl}methanol→1,3-Dihydro-1,3-dioxoisoindole→2-({4-[(4-fluorophenyl)methyl]morpholin-2-yl}methyl)-2,3-dihydro-1H-isoindole-1,3-dione→[(2R)-4-[(4-fluorophenyl)methyl]morpholin-2-yl]methanamine→4-Amino-5-chloro-2-ethoxybenzoic acid
Mosapride CitrateProcess routesteps: 4total yield: 363g(Mosapride Citrate (API))
Morpholin-2-ylmethanamine→4-Amino-5-chloro-2-ethoxybenzoic acid→4-Amino-5-chloro-2-ethoxy-N-(morpholin-2-ylmethyl)benzamide→4-Acetamido-5-chloro-2-ethoxy-N-[(morpholin-2-yl)methyl]benzamide→1-(Chloromethyl)-4-fluorobenzene→4-Acetamido-5-chloro-2-ethoxy-N-([4-[(4-fluorophenyl)methyl]morpholin-2-yl]methyl)benzamide
Mosapride CitrateOptimised routesteps: 4total yield: 53.87g(Mosapride Citrate-005)
4-Amino-5-chloro-2-ethoxybenzoic acid→Sodium 4-amino-2-hydroxybenzoate→Ethyl 1,3-dioxo-2-isoindolinecarboxylate→4-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-hydroxybenzoic acid→1-Bromoethane→Ethyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-ethoxybenzoate→Ethyl 5-chloro-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-ethoxybenzoate

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