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【结 构 式】 
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【分子编号】55637 【品名】2,6-Dihydroxybenzoic acid methyl ester; gamma-Resorcylic acid methyl ester 【CA登记号】2150-45-0 |
【 分 子 式 】C21H19N3O4 【 分 子 量 】377.39968 【元素组成】C 66.83% H 5.07% N 11.13% O 16.96% |
合成路线1
该中间体在本合成路线中的序号：(II)Fischer esterification of gamma-resorcylic acid (I) with EtOH and H2SO4 provided the ethyl ester (II). Subsequent Mitsunobu coupling of (II) with 1-tetradecanol (III) furnished ether (IV). The ethyl ester group of (IV) was finally hydrolyzed under basic conditions to yield the title carboxylic acid.
| 【1】 Kanojia, R.M.; Webb, G.; Krause, H.; Foleno, B.D.; Fernandez, J.; Bernstein, J.; Murray, W.; Lawrence, L.; Barrett, J.F.; 6-Oxa isosteres of anacardic acids as potent inhibitors of bacterial histidine protein kinase (HPK)-mediated two-component regulatory systems. Bioorg Med Chem Lett 1999, 9, 20, 2947. |
| 【2】 Kanojia, R.M.; Fernandez, J.; Foleno, B.D.; Murray, W.; Benstein, J.; Barret, J.F.; 6-Oxa isosteres of anacardic acids as potent inhibitors of bacterial histidine protein kinase (HPK)-mediated two-component regulatory systems. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 193. |
| 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) | 55636 | 2,6-Dihydroxybenzoic acid; gamma-Resorcylic acid; Resorcinol-2-carboxylic acid | 303-07-1 | C22H20N2O4S | 详情 | 详情 |
| (II) | 55637 | 2,6-Dihydroxybenzoic acid methyl ester; gamma-Resorcylic acid methyl ester | 2150-45-0 | C21H19N3O4 | 详情 | 详情 |
| (III) | 42819 | 1-tetradecanol | 112-72-1 | C14H30O | 详情 | 详情 |
| (IV) | 55638 | 2,6-dihydroxybenzoic acid | C7H6O4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VIII)6-Bromo-2-naphthylamine (II) was prepared from the corresponding naphthol (I) by treatment with ammonium hydroxide. Coupling of amine (II) with 4-[(methoxycarbonyl)methoxy]benzoic acid (III) by means of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) provided amide (IV). This was converted to nitrile (V) by displacement of the bromide with CuCN in hot 1,3-dimethyl-2-imidazolinone. Addition of H2S to the cyano group of (V) produced thioamide (VI), which was further alkylated with iodomethane to yield the thioimidate (VII). Amidine (VIII) was then prepared by treatment of (VII) with ammonium acetate. Finally, selective hydrolysis of the methyl ester group of (VIII) by means of NaOH gave rise to the title compound.
| 【1】 Yoshida, T.; Fukaya, C.; Inoue, Y.; Ashimori, A.; Kosaka, K.; Imada, T.; Nakamura, N.; Ono, S.; Preparation and pharmacological evaluation of novel glycoprotein (Gp) IIb/IIIa antagonists. 1. The selection of naphthalene derivatives. Chem Pharm Bull 1999, 47, 12, 1685. |
| 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) | 44398 | 6-bromo-2-naphthol | 15231-91-1 | C10H7BrO | 详情 | 详情 |
| (II) | 55631 | 6-bromo-2-naphthalenamine; 6-bromo-2-naphthylamine | 7499-66-3 | C10H8BrN | 详情 | 详情 |
| (III) | 55632 | 4-(2-methoxy-2-oxoethoxy)benzoic acid | C10H10O5 | 详情 | 详情 | |
| (IV) | 55633 | methyl 2-(4-{[(6-bromo-2-naphthyl)amino]carbonyl}phenoxy)acetate | C20H16BrNO4 | 详情 | 详情 | |
| (V) | 55634 | methyl 2-(4-{[(6-cyano-2-naphthyl)amino]carbonyl}phenoxy)acetate | C21H16N2O4 | 详情 | 详情 | |
| (VI) | 55635 | methyl 2-[4-({[6-(aminocarbothioyl)-2-naphthyl]amino}carbonyl)phenoxy]acetate | C21H18N2O4S | 详情 | 详情 | |
| (VII) | 55636 | 2,6-Dihydroxybenzoic acid; gamma-Resorcylic acid; Resorcinol-2-carboxylic acid | 303-07-1 | C22H20N2O4S | 详情 | 详情 |
| (VIII) | 55637 | 2,6-Dihydroxybenzoic acid methyl ester; gamma-Resorcylic acid methyl ester | 2150-45-0 | C21H19N3O4 | 详情 | 详情 |