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【结 构 式】

【分子编号】42889

【品名】4-toluic acid; 4-methylbenzoic acid

【CA登记号】99-94-5

【 分 子 式 】C8H8O2

【 分 子 量 】136.15032

【元素组成】C 70.57% H 5.92% O 23.5%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XIX)

In the third synthetic route, 3-methoxy-1-propyne (XVI) was isomerized to 1-methoxyallene (XVII) by means of potassium tert-butoxide and then treated with HCl to give 1-chloro-4-methoxy-2-butene (XVIII). Alkylation of the dilithio derivative of p-toluic acid (XIX) with chloride (XVIII) yielded (XX). Bromination of the enol ether (XX), followed by acid hydrolysis furnished bromo aldehyde (XXI). This was cyclized with tetraaminopyrimidine (XXII), affording the dihydropteridine (XXIII), which was subsequently dehydrogenated to pteridine (XXIV) employing KI3. The carboxylic acid group of (XXIV) was activated as the mixed anhydride (XXV) with isobutyl chloroformate and then coupled to aminoester (III), yielding amide (IX).

1 Rosowsky, A.; Vaidya, C.M.; Wright, J.E.; Forsch, R.A.; Bader, H.; Analogues of the potent nonpolyglutamatable antifolate Nalpha-(4-amino-4-deoxypteroyl)-Ndelta-hemiphthaloyl-L-ornithine (PT523) with modifications in the side chain, p-aminobenzoyl moiety, or 9,10-bridge: Synthesis and in vitro antitumor activity. J Med Chem 2000, 43, 8, 1620.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(III) 42875 methyl (2S)-2-amino-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentanoate C14H16N2O4 详情 详情
(IX) 42880 methyl (2S)-2-([4-[2-(2,4-diamino-6-pteridinyl)ethyl]benzoyl]amino)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentanoate C29H28N8O5 详情 详情
(XVI) 42888 3-methoxy-1-propyne; methyl 2-propynyl ether 627-41-8 C4H6O 详情 详情
(XVII) 19517 methyl 1,2-propadienyl ether; 1-methoxyallene C4H6O 详情 详情
(XVIII) 19518 (E)-3-chloro-1-propenyl methyl ether; (E)-3-chloro-1-methoxy-1-propene C4H7ClO 详情 详情
(XIX) 42889 4-toluic acid; 4-methylbenzoic acid 99-94-5 C8H8O2 详情 详情
(XX) 42890 4-[(E)-4-methoxy-3-butenyl]benzoic acid C12H14O3 详情 详情
(XXI) 42891 4-(3-bromo-4-oxobutyl)benzoic acid C11H11BrO3 详情 详情
(XXII) 19522 2,4,6-triamino-5-pyrimidinylamine; 2,4,5,6-pyrimidinetetramine 1004-74-6 C4H8N6 详情 详情
(XXIII) 42892 4-[2-(2,4-diamino-7,8-dihydro-6-pteridinyl)ethyl]benzoic acid C15H16N6O2 详情 详情
(XXIV) 42893 4-[2-(2,4-diamino-6-pteridinyl)ethyl]benzoic acid C15H14N6O2 详情 详情
(XXV) 42894   C20H22N6O4 详情 详情

合成路线2

该中间体在本合成路线中的序号:(I)

The title amide is obtained by condensation of 6-methylpyridine-3-carboxylic acid (I) with 4-ethoxy-2-nitroaniline by means of cyanuric chloride and TEA in dichloromethane.

1 Cai, S.X.; Drewe, J.A. (Cytovia, Inc.); Substd. nicotinamides and analogs as activators of caspases and inducers of apoptosis and the use thereof. WO 0155115 .
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) 42889 4-toluic acid; 4-methylbenzoic acid 99-94-5 C8H8O2 详情 详情
(II) 53589 2-Nitro-p-phenetidine; 4-Amino-3-nitrophenetole; 4-Ethoxy-2-nitroaniline; 4-Ethoxy-2-nitrobenzeneamine 616-86-4 C8H10N2O3 详情 详情
Extended Information