2-(5-cyano-1H-indol-1-yl)acetic acid -Drug Synthesis Database

【结构式】

【分子编号】31343

【品名】2-(5-cyano-1H-indol-1-yl)acetic acid

【CA登记号】

【分子式】C₁₁H₈N₂O₂

【分子量】200.1968

【元素组成】C 66% H 4.03% N 13.99% O 15.98%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

The alkylation of 5-cyanoindole (I) with methyl bromoacetate (II) in the presence of NaH in DMF provided the indolylacetate ester (III), which was hydrolyzed to the corresponding carboxylic acid (IV) with methanolic KOH. Coupling of (IV) with 4-benzylpiperidine (V) employing 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide-HCl (EDC) afforded amide (VI). Pinner reaction of (VI) with methanolic HCl produced imidate (VII), which was finally treated with ammonium carbonate in MeOH to yield the target amidine

参考文献中间体

合成目标

【1】 Duffy, D.E.; Dominguez, C.; Han, Q.; et al.; Design and synthesis of potent and selective 5,6-fused heterocyclic thrombin inhibitors. Bioorg Med Chem Lett 1999, 9, 7, 925.
【2】 Dominguez, C.; Han, Q.; Duffy, D.E.; Park, J.M.; Quan, M.L.; Rossi, K.A.; Wexler, R.R. (DuPont Pharmaceuticals Co.); Amidinoindoles, amidinoazoles, and analogs thereof as inhibitors of factor Xa and of thrombin. EP 0960102; WO 9801428 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	31341	5-Cyanoindole; Indole-5-carbonitrile; 1H-Indole-5-carbonitrile	15861-24-2	C₉H₆N₂	详情	详情
(II)	12309	methyl 2-bromoacetate; methyl bromoacetate	96-32-2	C₃H₅BrO₂	详情	详情
(III)	31342	methyl 2-(5-cyano-1H-indol-1-yl)acetate		C₁₂H₁₀N₂O₂	详情	详情
(IV)	31343	2-(5-cyano-1H-indol-1-yl)acetic acid		C₁₁H₈N₂O₂	详情	详情
(V)	26225	4-benzylpiperidine	31252-42-3	C₁₂H₁₇N	详情	详情
(VI)	31344	1-[2-(4-benzyl-1-piperidinyl)-2-oxoethyl]-1H-indole-5-carbonitrile		C₂₃H₂₃N₃O	详情	详情
(VII)	31345	methyl 1-[2-(4-benzyl-1-piperidinyl)-2-oxoethyl]-1H-indole-5-carboximidoate		C₂₄H₂₇N₃O₂	详情	详情

Extended Information