73954-34-4

Basic information

• Product Name: N-(2,2-dimethoxy-ethyl)-3,4-dimethoxyphenylacetamide
• Synonyms: N-(2,2-dimethoxy-ethyl)-3,4-dimethoxyphenylacetamide;N-(2,2-dimethoxyethyl)-2-(3,4-dimethoxyphenyl)acetamide;Ivabradine Impurity q;Ivabradine Impurity 19;N-(2,2-dimethoxyethyl)-2-(3,4-dimethoxyphenyl)acetamide(WXG00924)
• CAS NO: 73954-34-4
• Molecular Formula: C₁₄H₂₁NO₅
• Molecular Weight: 283.32024
• EINECS: 500-002-8
• Mol File: 73954-34-4.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 455.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.109±0.06 g/cm3(Predicted)
• PKA: 15.39±0.46(Predicted)
• CAS DataBase Reference: N-(2,2-dimethoxy-ethyl)-3,4-dimethoxyphenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,2-dimethoxy-ethyl)-3,4-dimethoxyphenylacetamide(73954-34-4)
• EPA Substance Registry System: N-(2,2-dimethoxy-ethyl)-3,4-dimethoxyphenylacetamide(73954-34-4)

Safety Data

• Hazardous Substances Data: 73954-34-4(Hazardous Substances Data)

Usage

Uses

N-(2,2-Dimethoxyethyl)-3,4-dimethoxybenzeneacetamide is an impurity of Ivabradine (I940500) which is used to treat angina pectoris and is a selective bradycardic agent with direct effect on the pacemaker If current of the sinoatrial node.

Upstream product

• 10313-60-7 3,4-dimethoxyphenylacetyl chloride 
• 22483-09-6 2,2-dimethoxyethylamine 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 5663-56-9 2-(3,4-dimethoxyphenyl)acetamide 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 

Downstream Products

• 1174715-26-4 N-(3,4-dimethoxyphenethyl)-2,2-dimethoxyethanamine 
• 1104967-34-1 3-[2-(3,4-dimethoxyphenyl)ethyl]-7,8-dimethoxy-1,3-dihydrobenzo[d]azepin-2-one 
• 148870-57-9 7,8-dimethoxy-3-[3-iodopropane]-1,3-dihydro-2H-3-benzazepin-2-one 
• 20925-64-8 7,8-dimethoxy-2-oxo-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 102226-97-1 N-[3-(7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-propyl]-3-(phenylamino)-propylamine 
• 102226-96-0 N-[3-(7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-propyl]-N-(3-phenylaminopropyl)-methylamine 
• 102226-84-6 N-[3-(7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-propyl]-N-(2-phenyloxyethyl)-methylamine 
• 148849-67-6 ivabradine hydrochloride 
• 1086026-31-4 3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one 
• 96255-05-9 7,8-Dimethoxy-3-(3-{methyl-[2-(3,4,5-trimethoxy-phenyl)-ethyl]-amino}-propyl)-1,3,4,5-tetrahydro-benzo[d]azepin-2-one 
• 96254-57-8 1-[7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-{2,4,6-trimethoxy-phenyl}-ethyl)-amino]-propane 
• 125846-71-1 Methanesulfonic acid 4-(2-{[3-(7,8-dimethoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-propyl]-methyl-amino}-ethyl)-phenyl ester 
• 125846-69-7 N-[3-(7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-propyl]-N-[4-(3,4-dimethoxyphenyloxy)-butyl]-methylamine 
• 96254-91-0 N-[3-(7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-propyl]-N-[2-(3,4-dimethoxyphenyl)-ethyl]-propylamine 

Relevant articles and documents

Design of oxa-spirocyclic PHOX ligands for the asymmetric synthesis of lorcaserin: Via iridium-catalyzed asymmetric hydrogenation

Phosphine-oxazoline (PHOX) ligands are a very important class of privileged ligands in asymmetric catalysis. A series of highly rigid oxa-spiro phosphine-oxazoline (O-SIPHOX) ligands based on O-SPINOL was synthesized efficiently, and their iridium complexes were synthesized by coordination of the O-SIPHOX ligands to [Ir(cod)Cl]2 in the presence of sodium tetrakis-3,5-bis(trifluoromethyl)phenylborate (NaBArF). The cationic iridium complexes showed high reactivity and excellent enantioselectivity in the asymmetric hydrogenation of 1-methylene-tetrahydro-benzo[d]azepin-2-ones (up to 99% yield and up to 99% ee). A key intermediate of the anti-obesity drug lorcaserin could be efficiently synthesized using this protocol.

PROCESS FOR THE PREPARATION OF BENZAZEPINE-2-ONE DERIVATIVE

The present, invention relates to a cost effective, environment friendly industrially viable process for the preparation of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepine-2-one, an intermediate used in the preparation of ivabradine, without using acid chloride intermediate and condensing agent.

Functional reversal of (?)-Stepholidine analogues by replacement of benzazepine substructure using the ring-expansion strategy

(?)-Stepholidine is an active ingredient of the Chinese herb Stephania and naturally occurring tetrahydroprotoberberine alkaloid with mixed dopamine receptor D1 agonistic and dopamine receptor D2 antagonistic activities. In this work, a series of novel hexahydrobenzo[4,5]azepino [2,1-a]isoquinolines were designed and synthesized as ring-expanded analogues of (?)-Stepholidine. Initial pharmacological assays demonstrated that a benzazepine replacement was associated with significant increase in selectivity and functional reversal at dopamine receptor D1. Compound-(?)-15e (Ki?=?5.32?±?0.01?nm) is more potent than (?)-Stepholidine (Ki?=?13?nm) and was identified as a selective dopamine receptor D1 antagonist (IC50?=?0.14?μm). Moreover, molecular modeling suggested that (?)-15e might exert its dopamine receptor D1 antagonistic activities through interacting with the transmembrane helix 7 of dopamine receptor D1.