“…Hydrolysis and regioselective decarboxylation with sulfuric acid (50%) followed by esterification gave the ethyl azaindole-2-carboxylate 10 in 72% yield. Employing a reductive amination protocol reported by Wright, this ester could be transformed into the piperazinylmethyl derivative 2 within a one-step process using LiAlH 4 in THF. 1 …”
mentioning
confidence: 99%
“…15 Hydrolysis and regioselective decarboxylation with sulfuric acid (50%) followed by esterification gave the ethyl azaindole-2-carboxylate 10 in 72% yield. Employing a reductive amination protocol reported by Wright, 16 this * To whom correspondence should be addressed. Tel: +49(9131)8529383.…”
Structure dependent efficacy studies in the field of selective D4 ligands led to the 2-aminomethyl substituted azaindole 2 (FAUC 213) that displayed strong D4 binding, high subtype selectivity, and complete antagonist properties in ligand-induced mitogenesis experiments. According to our schematic molecular model, the intrinsic activity of the regioisomers investigated is controlled by the ability of the heterocyclic unit to interact with both elements of the D4 binding-site crevice, the aromatic microdomain in TM6, and a serine residue in TM5.
“…Hydrolysis and regioselective decarboxylation with sulfuric acid (50%) followed by esterification gave the ethyl azaindole-2-carboxylate 10 in 72% yield. Employing a reductive amination protocol reported by Wright, this ester could be transformed into the piperazinylmethyl derivative 2 within a one-step process using LiAlH 4 in THF. 1 …”
mentioning
confidence: 99%
“…15 Hydrolysis and regioselective decarboxylation with sulfuric acid (50%) followed by esterification gave the ethyl azaindole-2-carboxylate 10 in 72% yield. Employing a reductive amination protocol reported by Wright, 16 this * To whom correspondence should be addressed. Tel: +49(9131)8529383.…”
Structure dependent efficacy studies in the field of selective D4 ligands led to the 2-aminomethyl substituted azaindole 2 (FAUC 213) that displayed strong D4 binding, high subtype selectivity, and complete antagonist properties in ligand-induced mitogenesis experiments. According to our schematic molecular model, the intrinsic activity of the regioisomers investigated is controlled by the ability of the heterocyclic unit to interact with both elements of the D4 binding-site crevice, the aromatic microdomain in TM6, and a serine residue in TM5.
“…It has long been recognised that the decomposition of excess LAH at the end of the reduction can play a significant role in the presence of products and by-products. The use of certain esters, such as ethyl acetate (EtOAc), can result in the alkylation of the amine [25][26][27]. For example, N-methyltryptamine derivatives (19) have been found to be converted to N-ethyl-N-methyltryptamines (20) by the addition of EtOAc during the LAH reaction of amide 18 (Fig.…”
“…Although more readily available than alkyl iodides, aldehydes or amides, carboxylic acids 10-14 and esters, [15][16][17] have been rarely employed to alkylate amines under reductive conditions. The need for a large excess of acid or ester was probably the major limitation of this reaction both for its use in synthesis and for its application to the preparation of [ 11 C]amines.…”
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