150007-96-8

Basic information

• Synonyms: Benzoic acid, 4-amino-5-chloro-2-methoxy-, anhydride with ethyl hydrogen carbonate (9CI)
• CAS NO: 150007-96-8
• Molecular Formula: C₁₁H₁₂ClNO₅
• Molecular Weight: 273.67
• Mol File: 150007-96-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N/A(CAS DataBase Reference)
• NIST Chemistry Reference: N/A(150007-96-8)
• EPA Substance Registry System: N/A(150007-96-8)

Safety Data

• Hazardous Substances Data: 150007-96-8(Hazardous Substances Data)

Upstream product

• 7206-70-4 4-amino-5-chloro-2-methoxybenzoic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 20896-27-9 methyl 4-amino-5-chloro-2-methoxybenzoate 

Downstream Products

• 122892-34-6 4-amino-5-chloro-N-<4-<2-(dimethylamino)ethoxy>benzyl>-2-methoxybenzamide 
• 61694-61-9 N-?[2-(n'-benzyl-N'-methylamino)ethyl]-4-amino-5-chloro-2-methoxybenzamide 
• 61694-35-7 N-[2-(n'-benzyl-N'-ethylamino)ethyl]-4-amino-5-chloro-2-methoxybenzamide 
• 61694-25-5 N-[2-(n'-ethyl-N'-p-methoxyphenylmethylamino)ethyl]-4-amino-5-chloro-2-methoxybenzamide 
• 61694-71-1 N-(1-benzyl-3-pyrrolidinyl)-4-amino-5-chloro-2-methoxybenzamide 
• 364-62-5 metoclopramide 
• 169451-72-3 (S)-(+)-4-amino-N-(1-benzyl-3-pyrrolidinyl)-5-chloro-2-methoxybenzamide 
• 287399-47-7 butyl 4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate 
• 81098-60-4 (+)-(3S,4R)-cisapride 
• 768370-78-1 4-(4-amino-5-chloro-2-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester 
• 61694-37-9 N-[2-(N',N'-dibenzylamino)ethyl]-4-amino-5-chloro-2-methoxy-benzamide 

Relevant articles and documents

An improved synthesis of butyl 4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate (AU-224)

A new and facile route for the synthesis of the novel gastrointestinal prokinetic butyl 4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate (1b), which exhibited potent gastro- and colon-prokinetic activities by oral administration without significant side effects, was established. The key intermediate, butyl 4-amino-1-piperidineacetate (16), was prepared from commercially available 4-amino-1-benzylpiperidine (2) in a high yield with four steps. Compound 1b was prepared by condensation of commercially available 4-amino-5-choloro-2-methoxybenzoic acid (7) with 16 in 84% yield. This improved synthetic route was appropriate for large-scale synthesis of 1b.

SYNTHESIS AND STRUCTURAL STUDY OF N-(8-ISOPROPYL-NORTROPAN-3-α-YL)-2-METHOXY-4-AMINO-5-CHLOROBENZAMIDE

N-(8-Isopropyl-nortropan-3-α-yl)-2-methoxy-4-amino-5-chlorobenzamide has been synthesized and its crystal and molecular structures determined by X-ray diffraction, IR, 1H-NMR and 13C-NMR methods.The pyrrolidine and piperidine rings adopt a flattened N-8 envelope and distorted chair conformation puckered at N-8 and flattened at C-3 respectively, with the N-isopropyl substituent and the amido group in axial position with respect to the piperidine ring.A great predominance in solution of the conformer observed in the solid state is proposed.

Improved synthesis and application of [11C]benzyl iodide in positron emission tomography radiotracer production

Positron emission tomography has increased the demand for new carbon-11 radiolabeled tracers and building blocks. A promising radiolabeling synthon is [11C]benzyl iodide ([11C]BnI), because the benzyl group is a widely present functi

Asymmetric syntheses of 3,4-syn- and 3,4-anti-3-substituted-4- aminopiperidin-2-ones: Application to the asymmetric synthesis of (+)-(3S,4R)-cisapride

The conjugate addition of lithium (R)-N-benzyl-N-(α-methylbenzyl) amide to δ-(N-allylamino)-α,β-unsaturated esters, followed by N-deallylation and cyclisation of the resultant β,δ-diamino esters, gives the corresponding 4-aminopiperidin-2-ones as single diastereoisomers (>99:1 dr). Subsequent deprotonation with LiHMDS and functionalisation of the resultant lithium enolate gives 3,4-anti-3-substituted-4-aminopiperidin-2-ones in >99:1 dr. Alternatively, in situ oxidation of the intermediate lithium (Z)-β-amino enolates formed upon conjugate addition gives α-hydroxy-β,δ-diamino esters, which after N-deallylation and cyclisation gives the corresponding 3,4-syn-3-hydroxy-4-aminopiperidin-2-ones in >99:1 dr. The utility of this methodology was successfully demonstrated in a concise asymmetric synthesis of the gastroprokinetic agent (+)-(3S,4R)- cisapride {(+)-(3S,4R)-N(1)-[3′-(4″-fluorophenoxy)propyl]-3-methoxy- 4-(2?-methoxy-4?-amino-5?-chlorobenzamido)piperidine} in nine steps from commercially available starting materials with an overall yield of 19%.

Synthesis and pharmacology of isoquinuclidine derivatives as 5-HT3 ligands

A series of 4-amino-5-chloro-2-methoxybenzoates and benzamides containing the 5- and 6-isoquinuclidinyl system was synthesised and evaluated for binding to 5-HT3, 5-HT4 and D2 receptors. In general, the isoquinuclidine derivatives at the 5-position have shown to be more potent as 5-HT3 ligands but they also possess 5-HT4 and D2 properties. However, the results show that the derivatives at the 6-position afforded the most promising compounds in terms of both receptor affinity and selectivity.

Synthesis and gastrointestinal prokinetic activity of novel benzamide derivatives with amphoteric side chains

Novel benzamide derivatives (19-24, 32a-c, 43d-f), each possessing a cycloaminoalkanecarboxylic acid side chain, were synthesized and their gastrointestinal prokinetic and dopamine D2 receptor antagonist activities were evaluated. 4-[(4-Amino-5

Serotoninergic properties of new conformationally restricted benzamides

A new series of benzamides derived from metoclopramide have been synthesized, in which the vicinal carbon of the basic nitrogen atom of the ethyl chain is situated on the C3, C4, C5 and C6 rings. The diamino derivatives were prepared through Strecker's reaction from the corresponding ketones except for the cyclopropyl derivatives where 1-ethoxy-1-trimethylsiloxy cyclopropane was used as the starting material. The benzamides were prepared using the mixed anhydride method. They were tested in binding assays for D2, 5-HT3 and 5-HT4 receptors. The results show a marked increase in the selectivity and potency of these derivatives for 5-HT3 receptors with regard to metoclopramide (compound 1d: 5-HT3 K(i) = 9.03 nM; 5-HT4 K(i) > 5000; D2 K(i) > 5000). The influences of steric hindrance and hydrophobic properties on the affinity of benzamide derivatives for 5-HT3 receptors were also emphasized by these data. The X-ray crystal structure of compound 1d was compared with that of the minimal energy conformer of BRL 24682, a reference 5-HT3 receptor antagonist benzamide, determined using the Random Search program. Superimposition of the two structures showed a suitable fit between the pharmacophore groups previously determined to be important for 5-HT3 receptor antagonists. On the other hand, the hydrophobic parts of the basic moieties had different spatial occupancies.

Dopamine D3 and D4 receptor antagonists: synthesis and structure--activity relationships of (S)-(+)-N-(1-Benzyl-3-pyrrolidinyl)-5-chloro-4- [(cyclopropylcarbonyl) amino]-2-methoxybenzamide (YM-43611) and related compounds.

In this study, we synthesized a series of (S)-N-(3-pyrrolidinyl)benzamide derivatives, 1, 2a-d, 5a-1, and 7, and their enantiomers, (R)-1 and (R)-5c-e, and evaluated their binding affinity for cloned dopamine D2, D3, and D4 receptors and their inhibitory

The Interaction of Ammonium, Sulfonium, and Sulfide Analogues of Metoclopramide with the Dopamine D2 Receptor

A series of permanently charged ammonium and sulfonium analogues of metoclopramide as well as a permanently uncharged sulfide analogue were synthesized and evaluated for their ability to inhibit apomorphine-induced responses on mouse striatal slices.Three of the four permanently charged analogues were found to inhibit apomorphine's effects, although at higher concentrations than either metoclopramide or its dimethyl analogue.In contrast, the sulfide analogue was inactive at concentrations up to 100 μM.These findings are consistent with earlier studies of chlorpromazine and sulpiride analogues and provide further evidence that dopamine antagonists bind in their charged molecular forms to anionic sites on the D2 receptor.Further, the results of this study in conjunction with those of our earlier sulpiride study would seem to indicate that differences in the biological profiles of metoclopramide, a type 1 benzamide useful as a gastric prokinetic agent, and sulpiride, a type 2 benzamide useful for its antipsychotic effects, are not due to any appreciable differences in the binding of the basic nitrogen atom of these molecules.

Synthesis, gastrointestinal prokinetic activity and structure-activity relationships of novel N-[[2-(dialkylamino)ethoxy]benzyl]benzamide derivatives

Novel N-[[2-(dialkylamino)ethoxy]benzyl]benzamide derivatives (II-1-51), derived from the structural modification of metoclopramide (1), were synthesized and examined for their pharmacological activities. Among them, N-[4-[2-(dimethylamino)ethoxy]benzyl]-3,4-dimethoxybenzamide (II-34) which exhibited well balanced gastrointestinal prokinetic and antiemetic activities was selected as a new type of gastrointestinal prokinetic agent.