5-aminonicotinic acid -Drug Synthesis Database

【结构式】

【分子编号】65053

【品名】5-aminonicotinic acid

【CA登记号】

【分子式】C₆H₆N₂O₂

【分子量】138.12592

【元素组成】C 52.17% H 4.38% N 20.28% O 23.17%

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：(XII)

5-Aminonicotinic acid (XII) is condensed with benzoyl isothiocyanate to form the benzoyl thiourea (XIII). Removal of the benzoyl group of (XIII) with NaOMe in MeOH, followed by alkylation with iodomethane, furnishes the S-methyl isothiourea (XIV). This is then condensed with 1,3-diamino-2-propanol (XV) in hot DMF, producing the tetrahydropyrimidine derivative (XVI). The carboxyl group of (XVI) is then activated as the mixed anhydride (XVII) employing isobutyl chloroformate and NMM. Coupling between anhydride (XVII) and amine (XI) in the presence of NMM leads to the diamide (XVIII). The ethyl ester group of (XVIII) is finally hydrolyzed by means of LiOH to the corresponding carboxylic acid.

参考文献中间体

合成目标

【1】 Miyashiro, J.M.; Gasiecki, A.F.; Khanna, I.K.; Chandrakumar, N.S.; Desai, B.N.; Russell, M.A.; Devadas, B.; Rico, J.G.; Rogers, T.E.; Rao, S.N.; Malecha, J.W.; Ruminski, P.G.; Yu, Y.; Huff, R. (Pfizer Inc.); Heterocyclic glycyl beta-alanine derivs. as vitronectin antagonists. EP 1070060; JP 2002511462; WO 9952896 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XI)	47974	ethyl (3S)-3-[(2-aminoacetyl)amino]-3-(3,5-dichloro-2-hydroxyphenyl)propanoate		C₁₃H₁₆Cl₂N₂O₄	详情	详情
(XII)	65053	5-aminonicotinic acid		C₆H₆N₂O₂	详情	详情
(XIII)	65054	5-{[(benzoylamino)carbothioyl]amino}nicotinic acid		C₁₄H₁₁N₃O₃S	详情	详情
(XIV)	65055	5-{[imino(methylsulfanyl)methyl]amino}nicotinic acid		C₈H₉N₃O₂S	详情	详情
(XV)	47975	1,3-diamino-2-propanol	616-29-5	C₃H₁₀N₂O	详情	详情
(XVI)	65056	5-[(5-hydroxy-1,4,5,6-tetrahydro-2-pyrimidinyl)amino]nicotinic acid		C₁₀H₁₂N₄O₃	详情	详情
(XVII)	65057			C₁₅H₂₀N₄O₅	详情	详情
(XVIII)	65058	ethyl (3S)-3-(3,5-dichloro-2-hydroxyphenyl)-3-({2-[({5-[(5-hydroxy-1,4,5,6-tetrahydro-2-pyrimidinyl)amino]-3-pyridinyl}carbonyl)amino]acetyl}amino)propanoate		C₂₃H₂₆Cl₂N₆O₆	详情	详情

Extended Information