carbonic dichloride -Drug Synthesis Database

【结构式】

【分子编号】56933

【品名】carbonic dichloride

【CA登记号】

【分子式】CCl₂O

【分子量】98.9158

【元素组成】C 12.14% Cl 71.68% O 16.17%

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：(III)

This compound has been obtained by two related ways: 1. The reaction of 5-diazoimidazole (I) with methylamine gives the triazene (II), which is then cyclized with 11C-phosgene (III) to yield the target 11C-carbonyl labeled compound. 2. The cyclization of 5-diazoimidazole-4-carboxamide (I) with 11C-carbonyl labeled methyl isocyanate (IV) gives the target 11C carbonyl labeled compound.

参考文献中间体

合成目标

【1】 Brock, C.S.; Brady, F.; Stevens, M.F.G.; Brown, G.D.; Price, P.M.; Luthra, S.K.; Antitumor imidazotetrazines. 40.(1) Radiosyntheses of [4-11C-carbonyl]- and 3-N-11C-methyl]-8-carbamoyl-3- methylimidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one (temozolomide) for positron emission tomography (PET) studies. J Med Chem 2002, 45, 25, 5448.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	56930	4-diazo-4H-imidazole-5-carboxamide	C₄H₃N₅O	详情	详情
(II)	56931	4-[(E)-3-methyl-2-triazenyl]-4H-imidazole-5-carboxamide	C₅H₈N₆O	详情	详情
(III)	56932	Carbonyl chloride	CCl₂O	详情	详情
(III)	56933	carbonic dichloride	CCl₂O	详情	详情
(IV)	11019	(Methylimino)(oxo)methane; methyl isocyanate	C₂H₃NO	详情	详情
(IV)	56934	(methylimino)(oxo)methane; methyl isocyanate	C₂H₃NO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VII)

The reaction of 4-amino-1-naphthol (I) with Boc2O in THF gives the carbamate (II), which is condensed with 4-(2-chloroethyl)morpholine (III) by means of K2CO3 in hot acetonitrile to yield ether (IV). The hydrolysis of the carbamate group of (IV) by means of HCl in dioxane affords the naphthylamine (V), which is finally condensed with 3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amine (VI) and phosgene (VII) in THF to provide the target urea. The intermediates 3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amine (VI) and phosgene (VII) are obtained by cyclization of 4-methylphenylhydrazine (VIII) with 4,4-dimethyl-3-oxopentanenitrile (IX) in refluxing toluene or by means of HCl in refluxing ethanol.

参考文献中间体

合成目标

【1】 Regan, J.; et al.; Pyrazole urea-based inhibtitors of p38 MAP kinase: From lead compound to clinical candidate. J Med Chem 2002, 45, 14, 2994.

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)	55430	4-Amino-1-naphthol		C₁₀H₉NO	详情	详情
(II)	55431	tert-butyl 4-hydroxy-1-naphthylcarbamate		C₁₅H₁₇NO₃	详情	详情
(III)	27355	4-(2-chloroethyl)morpholine	3647-69-6	C₆H₁₂ClNO	详情	详情
(IV)	55432	tert-butyl 4-[2-(4-morpholinyl)ethoxy]-1-naphthylcarbamate		C₂₁H₂₈N₂O₄	详情	详情
(V)	55427	4-[2-(4-morpholinyl)ethoxy]-1-naphthalenamine; 4-[2-(4-morpholinyl)ethoxy]-1-naphthylamine		C₁₆H₂₀N₂O₂	详情	详情
(VI)	55425	3-(tert-butyl)-1-(4-methylphenyl)-1H-pyrazol-5-amine; 3-(tert-butyl)-1-(4-methylphenyl)-1H-pyrazol-5-ylamine		C₁₄H₁₉N₃	详情	详情
(VII)	56933	carbonic dichloride		CCl₂O	详情	详情
(VIII)	20387	1-(4-methylphenyl)hydrazine		C₇H₁₀N₂	详情	详情
(IX)	44248	4,4-dimethyl-3-oxopentanenitrile	59997-51-2	C₇H₁₁NO	详情	详情

合成路线3

该中间体在本合成路线中的序号：(IV)

The cyclization of the acridinonecarboxamide (I) with N-[2-(1-piperidinyl)ethyl]hydrazine (II) in 2-ethoxyethanol at 120 C gives the pyrazoloacridine (III) (1), which is cyclized with phosgene (IV) in chloroform at room temperature to afford the target pentacyclic compound.

参考文献中间体

合成目标

【1】 Antonini, I.; et al.; Synthesis, antitumor cytotoxicity, and DNA-binding of novel N-5,2-Di(omega-aminoalkyl)-2,6-dihydropyrazolo[3,4,5-kl) acridine-5-carboxamides. J Med Chem 2001, 44, 20, 3329.
【2】 Polucci, P.; Pescalli, N.; Menta, E.; Antonini, I.; Gatto, B.; Martelli, S.; Magnano, A.; Palumbo, M.; 2,6-Di(omega-aminoalkyl)-2,5,6,7-tetrahydopyrazolo[3,4,5-mn]pyrimido[5,6,1-de]acridine-5,7-diones: Novel, potent, cytotoxic, and DNA-binding agents. J Med Chem 2002, 45, 3, 696.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	59362	N-[2-(dimethylamino)ethyl]-7-methoxy-9-oxo-9,10-dihydro-4-acridinecarboxamide	C₁₉H₂₁N₃O₃	详情	详情
(II)	59363	1-(2-hydrazinoethyl)piperidine	C₇H₁₇N₃	详情	详情
(III)	59364	N-[2-(dimethylamino)ethyl]-9-methoxy-2-[2-(1-piperidinyl)ethyl]-2,6-dihydropyrazolo[3,4,5-kl]acridine-5-carboxamide	C₂₆H₃₄N₆O₂	详情	详情
(IV)	56933	carbonic dichloride	CCl₂O	详情	详情

Extended Information