disodium 4-amino-1,7-naphthalenedisulfonate -Drug Synthesis Database

【结构式】

【分子编号】27851

【品名】disodium 4-amino-1,7-naphthalenedisulfonate

【CA登记号】

【分子式】C₁₀H₇NNa₂O₆S₂

【分子量】347.280256

【元素组成】C 34.59% H 2.03% N 4.03% Na 13.24% O 27.64% S 18.47%

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：(I)

The reaction of 4-aminonaphthalene-1,7-disulfonic acid disodium salt (I) with 1-methyl-4-nitropyrrole-2-carbonyl chloride (II) by means of NaOAc in water gives the corresponding nitro-amide (III), which is reduced with H2 over Pd/C in water to the amino-amide (IV). The reaction of (IV) with 4-nitropyrrole-2-carbonyl chloride (V) by means of NaOH and NaOAc yields the nitro-diamide (VI), which is reduced with H2 over Pd/C as before affording the amino-diamide (VII). Finally, this compound is dimerized by reaction with phosgene and KOAc in dioxane/water.

参考文献中间体

合成目标

【1】 Bigelow, J.; Oppenheim, J.J.; Rice, W.G.; Buckheit, R.W.; Covey, J.M.; Howard, O.M.Z.; Clanton, D.J.; McCormack, J.J.; Hollisgshead, M.G.; Turpin, J.A.; Inhibition of in vitro and in vivo HIV replication by a distamycin analogue that interferes with chemokine receptor function: A candidate for chemotherapeutic and microbicidal application. J Med Chem 1998, 41, 13, 2184.
【2】 Mongelli, N.; Biasoli, G.; Paio, A.; Grandi, M.; Ciomei, M. (Pharmacia Corp.); New ureido derivs. of poly-4-amino-2-carboxy-1-methyl cpds.. EP 0462258; JP 1992504426; US 5260329; US 5420296; WO 9110649 .

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)	27851	disodium 4-amino-1,7-naphthalenedisulfonate		C₁₀H₇NNa₂O₆S₂	详情	详情
(II)	27852	1-methyl-4-nitro-1H-pyrrole-2-carbonyl chloride		C₆H₅ClN₂O₃	详情	详情
(III)	27853	disodium 4-[[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino]-1,7-naphthalenedisulfonate		C₁₆H₁₁N₃Na₂O₉S₂	详情	详情
(IV)	27854	4-nitro-1H-pyrrole-2-carbonyl chloride		C₅H₃ClN₂O₃	详情	详情
(V)	27855	disodium 4-[[(1-methyl-4-[[(4-nitro-1H-pyrrol-2-yl)carbonyl]amino]-1H-pyrrol-2-yl)carbonyl]amino]-1,7-naphthalenedisulfonate		C₂₁H₁₅N₅Na₂O₁₀S₂	详情	详情
(VI)	27856	disodium 4-[[(4-[[(4-amino-1H-pyrrol-2-yl)carbonyl]amino]-1-methyl-1H-pyrrol-2-yl)carbonyl]amino]-1,7-naphthalenedisulfonate		C₂₁H₁₇N₅Na₂O₈S₂	详情	详情
(VII)	27857	4-(1,1,2,2-tetrafluoroethoxy)aniline	713-62-2	C₈H₇F₄NO	详情	详情

Extended Information