(E)-1-Bromo-6,6-dimethyl-2-hepten-4-yne -Drug Synthesis Database

【结构式】

【分子编号】10109

【品名】(E)-1-Bromo-6,6-dimethyl-2-hepten-4-yne

【CA登记号】78629-21-7

【分子式】C₉H₁₃Br

【分子量】201.10622

【元素组成】C 53.75% H 6.52% Br 39.73%

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：(V)

1) The Grignard reaction of 1-bromonaphthalene (I) with Mg in THF and then with [14C]-labeled CO2 gives the corresponding 1-naphthoic acid (II), which by reaction with SO2Cl2 and then with methylamine yields [14C]-N-methyl-1-naphthalenecarboxamide (III). The reduction of (III) with LiAlH4 in refluxing THF affords the corresponding amine (IV). Finally, this compound is condensed with 1-bromo-6,6-dimethylhept-2-en-4-yne (V) by means of Na2CO3 in DMF, and treated with ethanolic HCl.

参考文献中间体

合成目标

【1】 Andres, H.; Carbon-14 labelling of terbinafine, an antimycotic agent. J Label Compd Radiopharm 1989, 27, 11, 1307.

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)	10105	1-Bromonaphthalene	90-11-9	C₁₀H₇Br	详情	详情
(II)	10106	1-Naphthoic acid	86-55-5	C₁₁H₈O₂	详情	详情
(II)	44581	1-naphthoic acid		C₁₁H₈O₂	详情	详情
(III)	10107	N-Methyl-1-naphthamide	3400-33-7	C₁₂H₁₁NO	详情	详情
(III)	44582	N-methyl-1-naphthamide		C₁₂H₁₁NO	详情	详情
(IV)	10108	N-Methyl(1-naphthyl)methanamine; N-Methyl-N-(1-naphthylmethyl)amine; 1-Methyl-1-naphthalenemethylamine	65473-13-4	C₁₂H₁₃N	详情	详情
(IV)	44583	N-methyl(1-naphthyl)methanamine; N-methyl-N-(1-naphthylmethyl)amine		C₁₂H₁₃N	详情	详情
(V)	10109	(E)-1-Bromo-6,6-dimethyl-2-hepten-4-yne	78629-21-7	C₉H₁₃Br	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

A new synthesis of SDZ-87469 has been published: The chlorination of 7-methylbenzo[b]thiophene (I) gives 2,3-dichloro-7-methylbenzo[b]thiophene (II), which is selectively dechlorinated with butyllithium and hydrolysis, yielding 3-chloro-7-methylbenzo[b]thiophene (III). The bromination of (III) with N-bromosuccinimide (NBS) in DMF affords 7-(bromomethyl)-3-chlorobenzo[b]thiophene (IV), which is finally condensed with N,6,6-trimethylhep-2-en-4-yn-1-amine (V) (E + Z mixture) by means of K2CO3 in DMF. The pure E-isomer is obtained by crystallization of the E + Z mixture of the hydrochlorides in ethanol. Amine (V) is obtained by reaction of the corresponding bromo derivative (IV) with methylamine.

参考文献中间体

合成目标

【1】 Petranyi, G.; Stutz, A.; J Med Chem 1984, 27, 12, 1539-43.
【2】 Stutz, A.; Nussbaumer, P.; Rev Iberoam Micol 1988, 5, 1, 89.
【3】 Loozen, H.; Godefroi, E.; J Org Chem 1973, 38, 5, 1056-7.
【4】 Stutz, A. (Novartis Deutschland GmbH); New allylamines and their use.. DE 3302814 .
【5】 Nussbaumer, P.; Petranyi, G.; Stutz, A.; Synthesis and structure-activity relationships of benzo[b]thienylallylamine antimycotics. J Med Chem 1991, 34, 1, 65-73.

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)	12835	7-Methyl-1-benzothiophene		C₉H₈S	详情	详情
(II)	12836	2,3-Dichloro-7-methyl-1-benzothiophene		C₉H₆Cl₂S	详情	详情
(III)	12837	3-Chloro-7-methyl-1-benzothiophene		C₉H₇ClS	详情	详情
(IV)	12838	7-(Bromomethyl)-3-chloro-1-benzothiophene		C₉H₆BrClS	详情	详情
(V)	12839	N-[(E)-6,6-Dimethyl-2-hepten-4-ynyl]-N-methylamine; (E)-N,6,6-Trimethyl-2-hepten-4-yn-1-amine		C₁₀H₁₇N	详情	详情
(VI)	10109	(E)-1-Bromo-6,6-dimethyl-2-hepten-4-yne	78629-21-7	C₉H₁₃Br	详情	详情

Extended Information