48740-RP, RP-48740
3-(3-吡啶基)-1H,3H-吡咯并[1,2-c]噻唑-7-甲酰胺Chemical Name: 3-(3-Pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxamide
CAS No. 93363-11-2
项目整合开发状态: Phase II
项目研究机构: Aventis Pharma (Originator)
合成路线:The cyclization of pyridine-3-carbaldehyde (II) with L-cysteine (I) in ethanol gives the thiazolidine derivative (III),which is treated with formic acid yielding the 3-formylthiazolidine derivative (IV).The cyclization of (IV) with 2-chloropropenenitrile (V) by means of acetic anhydride affords 3-(3-pyridil)-1H,3H-pyrrolo[1,2-c]thiazole-7-carbonitrile (VI),which is finally hydrolyzed to the target carboxamide by means of KOH in tert-butanol.
📌 参考资料/链接：
参考文献标题:Novel 1H,3H-pyrrolo[1,2-c]thiazole derivs.,their preparation and medicaments containing them
文献作者:Fabre,J.-L.; Farge,D.; James,C.; Lav? D.(Aventis SA)
参考来源:EP 0115979; US 4529728
📄 详细内容
合成路线:The cyclization of pyridine-3-carbaldehyde (II) with L-cysteine (I) in ethanol gives the thiazolidine derivative (III),which is treated with formic acid yielding the 3-formylthiazolidine derivative (IV).The cyclization of (IV) with 2-chloropropenenitrile (V) by means of acetic anhydride affords 3-(3-pyridil)-1H,3H-pyrrolo[1,2-c]thiazole-7-carbonitrile (VI),which is finally hydrolyzed to the target carboxamide by means of KOH in tert-butanol.
合成路线:The cyclization of pyridine-3-carbaldehyde (II) with L-cysteine (I) in ethanol gives the thiazolidine derivative (III),which is treated with formic acid,yielding a diastereomeric mixture of formyl derivatives from which the desired (2R,4R)-(IV) is isolated by crystallization.The cyclization of (2R,4R)-(IV) with ethyl 2,3-dichloropropionate (V) by means of TsCl and Et3N affords (2R)-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxylic acid ethyl ester (VI),which is hydrolyzed with NaOH to the corresponding free acid (VII).Finally,this compound is condensed with 3-aminobenzophenone (VIII) by means of SOCl2 to provide the target amide.
参考文献标题:PYRROLO[1,2-c]THIAZOLE DERIVATIVES: POTENT PAF RECEPTOR ANTAGONISTS
文献作者:Lav? D.; James,C.; Rajoharison,H.; Bost,P.E.; Cavero,I.
参考来源:Drugs Fut 1989,14(9),891
产品链接: CAS No. 93363-11-2››