5-(dimethylamino)-1-naphthalenesulfonyl chloride -Drug Synthesis Database

【结构式】

【分子编号】19027

【品名】5-(dimethylamino)-1-naphthalenesulfonyl chloride

【CA登记号】605-65-2

【分子式】C₁₂H₁₂ClNO₂S

【分子量】269.75152

【元素组成】C 53.43% H 4.48% Cl 13.14% N 5.19% O 11.86% S 11.89%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

Bromination of 2-amino-5-chloropyrazine (I) with bromine in chloroform-pyridine provided bromopyrazine (II). Then, reaction with sodium methoxide in refluxing methanol afforded methyl ether (III). Finally, condensation of (III) with dansyl chloride (IV) in the presence of NaH in dimethoxyethane yielded the corresponding sulfonamide.

参考文献中间体

合成目标

【1】 Hunt, S.J.; Tang, E.K.; James, R.; Heys, C.; Sumner, N.F.; Whiting, E.; Telford, B.; Dennis, M.; Mortlock, A.A.; Bath, C.; Wilson, C.; Butlin, R.J.; Bradbury, R.H.; New non-peptide endothelin-A receptor antagonists: Synthesis, biological properties, and structure-activity relationships of 5-(dimethylamino)-N-pyridyl-, -N-pyrimidinyl-, -N-pyridazinyl-, and -N-pyrazinyl-1-naphthalenesulfonamides. J Med Chem 1997, 40, 6, 996.
【2】 Bradbury, R.H. (AstraZeneca plc); N-Heterocyclyl sulphonamide derivs. and their use as endothelin antagonists. EP 0752986; JP 1997510987; US 6083951; WO 9526957 .

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)	19024	5-chloro-2-pyrazinylamine; 5-chloro-2-pyrazinamine		C₄H₄ClN₃	详情	详情
(II)	19025	3-bromo-5-chloro-2-pyrazinylamine; 3-bromo-5-chloro-2-pyrazinamine		C₄H₃BrClN₃	详情	详情
(III)	19026	5-chloro-3-methoxy-2-pyrazinylamine; 5-chloro-3-methoxy-2-pyrazinamine		C₅H₆ClN₃O	详情	详情
(IV)	19027	5-(dimethylamino)-1-naphthalenesulfonyl chloride	605-65-2	C₁₂H₁₂ClNO₂S	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 reaction of 5-(dimethylamino)naphthalene-1-sulfonyl chloride (I) with 4-nitroaniline (II) in pyridine gives the corresponding sulfonamide (III), which is reduced at the nitro group with hydrogen over Pd/C in ethanol, yielding the expected amine (IV). Finally, this compound is condensed with 3-hydroxy-2,2-dimethylpropionic acid (V) by means of propylphosphonic anhydride (PRPA) and triethylamine in dichloromethane/ethyl acetate.

参考文献中间体

合成目标

【1】 Hallenberger, S.; Weber, O.; Bender, W.; Eckenberg, P.; Reefschlaeger, J.; Goldmann, S.; Trappe, J.; Haerter, M.; A novel nonnucleosidic inhibitor of human cytomegalovirus replication. Intersci Conf Antimicrob Agents Chemother 1999, Abst F940.
【2】 Leeson, P.A.; Sorbera, L.A.; Castañer, J.; Bay-38-4766. Drugs Fut 1999, 24, 12, 1297.
【3】 Trappe, J.; Weber, O.; Eckenberg, P.; Hallenberger, S.; Bender, W.; Goldmann, S.; Harter, M.; Reefschlager, J. (Bayer AG); Novel naphthyl-substd. and anilide-substd. sulfonamides. WO 9937609 .

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)	19027	5-(dimethylamino)-1-naphthalenesulfonyl chloride	605-65-2	C₁₂H₁₂ClNO₂S	详情	详情
(II)	15547	4-nitrophenylamine; p-Nitroaniline; 4-nitroaniline	100-01-6	C₆H₆N₂O₂	详情	详情
(III)	30616	5-(dimethylamino)-N-(4-nitrophenyl)-1-naphthalenesulfonamide		C₁₈H₁₇N₃O₄S	详情	详情
(IV)	30617	N-(4-aminophenyl)-5-(dimethylamino)-1-naphthalenesulfonamide		C₁₈H₁₉N₃O₂S	详情	详情
(V)	30618	3-hydroxy-2,2-dimethylpropionic acid	4835-90-9	C₅H₁₀O₃	详情	详情

Extended Information