4-(1,1,2,2-tetrafluoroethoxy)aniline -Drug Synthesis Database

【结构式】

【分子编号】27857

【品名】4-(1,1,2,2-tetrafluoroethoxy)aniline

【CA登记号】713-62-2

【分子式】C₈H₇F₄NO

【分子量】209.1433328

【元素组成】C 45.94% H 3.37% F 36.34% N 6.7% O 7.65%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(I)

Aniline (I) was converted to phenyl carbamate (II) by treatment with phenyl chloroformate. Subsequent condensation of (III) with 2,2-diethoxyethylamine provided urea (III), which was cyclized under acidic conditions to give imidazolone (IV). Optionally, imidazolidinone (V) was obtained by catalytic hydrogenation of (IV).

参考文献中间体

合成目标

【1】 Itoh, K.; Tamura, N.; Matsushita, Y.; Hososno, H.; Hayashi, R.; Okonogi, K.; Kitazaki, T.; Tasaka, A.; Optically active antifungal azoles. VIII. Synthesis and antifungal activity of 1-[(1R,2R)-2-(2,4-difluoro- and 2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-(4-substituted phenyl)-2(1H,3H)-imidazolones and 2-imidazolidinones. Chem Pharm Bull 1999, 47, 3, 351.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10331	2,2-Diethoxy-1-ethanamine; 2,2-Diethoxyethylamine; Aminoacetaldehyde diethyl acetal	645-36-3	C₆H₁₅NO₂	详情	详情
	13580	1-[(Chlorocarbonyl)oxy]benzene; phenyl chloroformate	1885-14-9	C₇H₅ClO₂	详情	详情
(I)	27857	4-(1,1,2,2-tetrafluoroethoxy)aniline	713-62-2	C₈H₇F₄NO	详情	详情
(II)	27858	phenyl 4-(1,1,2,2-tetrafluoroethoxy)phenylcarbamate		C₁₅H₁₁F₄NO₃	详情	详情
(III)	27859	N-(2,2-diethoxyethyl)-N'-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]urea		C₁₅H₂₀F₄N₂O₄	详情	详情
(IV)	27860	1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-1,3-dihydro-2H-imidazol-2-one		C₁₁H₈F₄N₂O₂	详情	详情
(V)	27861	1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2-imidazolidinone		C₁₁H₁₀F₄N₂O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Aniline (I) was converted to phenyl carbamate (II) by treatment with phenyl chloroformate. Subsequent condensation of (II) with 2,2-diethoxyethylamine provided urea (III), which was cyclized under acidic conditions to give imidazolone (IV). Optionally, imidazolidinone (V) was obtained by catalytic hydrogenation of (IV).

参考文献中间体

合成目标

【1】 Itoh, K.; Tamura, N.; Matsushita, Y.; Hososno, H.; Hayashi, R.; Okonogi, K.; Kitazaki, T.; Tasaka, A.; Optically active antifungal azoles. VIII. Synthesis and antifungal activity of 1-[(1R,2R)-2-(2,4-difluoro- and 2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-(4-substituted phenyl)-2(1H,3H)-imidazolones and 2-imidazolidinones. Chem Pharm Bull 1999, 47, 3, 351.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10331	2,2-Diethoxy-1-ethanamine; 2,2-Diethoxyethylamine; Aminoacetaldehyde diethyl acetal	645-36-3	C₆H₁₅NO₂	详情	详情
	13580	1-[(Chlorocarbonyl)oxy]benzene; phenyl chloroformate	1885-14-9	C₇H₅ClO₂	详情	详情
(I)	27857	4-(1,1,2,2-tetrafluoroethoxy)aniline	713-62-2	C₈H₇F₄NO	详情	详情
(II)	27858	phenyl 4-(1,1,2,2-tetrafluoroethoxy)phenylcarbamate		C₁₅H₁₁F₄NO₃	详情	详情
(III)	27859	N-(2,2-diethoxyethyl)-N'-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]urea		C₁₅H₂₀F₄N₂O₄	详情	详情
(IV)	27860	1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-1,3-dihydro-2H-imidazol-2-one		C₁₁H₈F₄N₂O₂	详情	详情
(V)	27861	1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2-imidazolidinone		C₁₁H₁₀F₄N₂O₂	详情	详情

合成路线3

该中间体在本合成路线中的序号：(VII)

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