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【结 构 式】

【分子编号】65056

【品名】5-[(5-hydroxy-1,4,5,6-tetrahydro-2-pyrimidinyl)amino]nicotinic acid

【CA登记号】

【 分 子 式 】C10H12N4O3

【 分 子 量 】236.23044

【元素组成】C 50.84% H 5.12% N 23.72% O 20.32%

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:(XVI)

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.

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