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CAS 171489-59-1

methyl (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

Codes: TADA-006

Application context (from source-drug indications)

Erectile dysfunctionTadalafil/TamsulosinBenign prostatic hyperplasiaTadalafil/TamsulosinErectile dysfunctionAmlodipine Besylate/TadalafilHypertensionAmlodipine Besylate/TadalafilBenign prostatic hyperplasiaTadalafilPulmonary hypertensionTadalafilPulmonary arterial hypertensionTadalafilErectile dysfunctionTadalafilPremature ejaculationTadalafilGenitourinary neoplasmTadalafil

Source drugs (routes using this intermediate)

DrugTierExpiry
Tadalafil/TamsulosinTier C — Watch / trade-
Amlodipine Besylate/TadalafilTier C — Watch / trade-
TadalafilTier 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.

Tadalafil/TamsulosinOptimised routesteps: 6total yield: /
methyl (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl L-tryptophanate hydrochloride→methyl (1S,3S)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl (1S,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(4-nitrobenzyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl (1S,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl (1S,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride
Tadalafil/TamsulosinOptimised routesteps: 3total yield: /
benzo[d][1,3]dioxole-5-carbaldehyde→methyl (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl D-tryptophanate
Amlodipine Besylate/TadalafilOptimised routesteps: 6total yield: /
methyl (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl L-tryptophanate hydrochloride→methyl (1S,3S)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl (1S,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(4-nitrobenzyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl (1S,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl (1S,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride
Amlodipine Besylate/TadalafilOptimised routesteps: 3total yield: /
benzo[d][1,3]dioxole-5-carbaldehyde→methyl (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl D-tryptophanate
TadalafilOptimised routesteps: 6total yield: /
methyl (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl L-tryptophanate hydrochloride→methyl (1S,3S)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl (1S,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(4-nitrobenzyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl (1S,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl (1S,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride
TadalafilOptimised routesteps: 3total yield: /
benzo[d][1,3]dioxole-5-carbaldehyde→methyl (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate→methyl D-tryptophanate

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