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【结 构 式】

【分子编号】10108

【品名】N-Methyl(1-naphthyl)methanamine; N-Methyl-N-(1-naphthylmethyl)amine; 1-Methyl-1-naphthalenemethylamine

【CA登记号】65473-13-4

【 分 子 式 】C12H13N

【 分 子 量 】171.24196

【元素组成】C 84.17% H 7.65% N 8.18%
与该中间体有关的原料药合成路线共 9 条
合成路线1合成路线2合成路线3合成路线4合成路线5合成路线6合成路线7合成路线8合成路线9

合成路线1

该中间体在本合成路线中的序号：(IV)

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：(IV)

The condensation of N-(1-naphthylmethyl)methylamine (IV) with formaldehyde and 5,5-dimethylhexadiine (V) by means of Cu2Cl2 also gives (III), which is then reduced selectively with diisobutylaluminum hydride in toluene.

参考文献 中间体
合成目标
【1】 Stutz, A.; SF-86327 and related compounds: Synthetic methods. Int Con Chemother 1983, 116, 5-8.
【2】 Serradell, M.N.; Castaner, J.; SF-86327. Drugs Fut 1984, 9, 6, 425.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(III) 30535 N-(6,6-dimethyl-2,4-heptadiynyl)-N-methyl-N-(1-naphthylmethyl)amine; N,6,6-trimethyl-N-(1-naphthylmethyl)-2,4-heptadiyn-1-amine C21H23N 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
(V) 30536 5,5-dimethyl-1,3-hexadiyne C8H10 详情 详情

合成路线3

该中间体在本合成路线中的序号：(IV)

By reductocondensation of amino (IV) with 6,6-dimethylhept-2-en-4-ynal (VI) by means of NaBH4 in methanol.

参考文献 中间体
合成目标
【1】 Stutz, A. (Novartis AG); Propenylamines, pharmaceutical compositions containing them and their use as pharmaceuticals. EP 0024587; JP 56032440; JP 63313753; Us 4755534 .
【2】 Serradell, M.N.; Castaner, J.; SF-86327. Drugs Fut 1984, 9, 6, 425.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(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
(VI) 30357 4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carbohydrazide C17H22N4O 详情 详情

合成路线4

该中间体在本合成路线中的序号：(IV)

The condensation of propenal (VII) with tert-butylacetylene (VIII) by means of butyllithium gives 6,6-dimethylhept-1-en-4-yn-3-ol (IX), which is rearranged with HBr to the allyl isomer 6,6-dimethylhept-2-en-4-yn-1-yl bromide (X). Finally, this compound is condensed with amine (IV) by means of Na2CO3 in DMF.

参考文献 中间体
合成目标
【1】 Stutz, A.; SF-86327 and related compounds: Synthetic methods. Int Con Chemother 1983, 116, 5-8.
【2】 Stutz, A. (Novartis AG); Propenylamines, pharmaceutical compositions containing them and their use as pharmaceuticals. EP 0024587; JP 56032440; JP 63313753; Us 4755534 .
【3】 Serradell, M.N.; Castaner, J.; SF-86327. Drugs Fut 1984, 9, 6, 425.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(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
(VII) 17668 acrylaldehyde; Acrolein 107-02-8 C3H4O 详情 详情
(VIII) 30538 4,4-dimethyl-2-pentyne 999-78-0 C7H12 详情 详情
(IX) 30539 6,6-dimethyl-1-hepten-4-yn-3-ol C9H14O 详情 详情
(X) 30540 (E)-1-bromo-5,5-dimethyl-1-hexen-3-yne C8H11Br 详情 详情

合成路线5

该中间体在本合成路线中的序号：(II)

By condensation of cyannamyl chloride (I) with methyl (1-naphtylmethyl)amine (II) by means of Na2CO3 in DMF.

参考文献 中间体
合成目标
【1】 Berney, D.; Process for the preparation of novel N-(3-phenyl-2-propenyl)naphthylmethylamines. BE 0853976; CH 620896; JP 61171416 .
【2】 Castaner, J.; Blancafort, P.; Serradell, M.N.; Naftifungin. Drugs Fut 1980, 5, 3, 141.
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) 32678 1-[(E)-3-chloro-1-propenyl]benzene 21087-29-6 C9H9Cl 详情 详情
(II) 10108 N-Methyl(1-naphthyl)methanamine; N-Methyl-N-(1-naphthylmethyl)amine; 1-Methyl-1-naphthalenemethylamine 65473-13-4 C12H13N 详情 详情

合成路线6

该中间体在本合成路线中的序号：(I)

By condensation of N-methyl-1-naphthylmethylamine (I) with 4-(tert-butyl)benzyl bromide (II) by means of Na2CO3 in DMF, followed by acidification with HCl in ethanol.

参考文献 中间体
合成目标
【1】 Arai, K.; Arita, M.; Sedino, T.; Komoto, N.; Hirose, S. (Mitsui Toatsu Chem.; Inc.); Benzylamine derivatives, process for production thereof, and use thereof. EP 0221781 .
【2】 Prous, J.; Castaner, J.; KP-363. Drugs Fut 1989, 14, 4, 315.
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) 10108 N-Methyl(1-naphthyl)methanamine; N-Methyl-N-(1-naphthylmethyl)amine; 1-Methyl-1-naphthalenemethylamine 65473-13-4 C12H13N 详情 详情
(II) 20588 1-(bromomethyl)-4-(tert-butyl)benzene 18880-00-7 C11H15Br 详情 详情

合成路线7

该中间体在本合成路线中的序号：(IV)

The intermediate naphthylmethyl amine (IV) was prepared from 1-naphthaldehyde (I) by two related procedures. Reduction of (II) with NaBH4 gave alcohol (II), which was converted to the corresponding chloride with SOCl2 and then condensed with methylamine. Alternatively, condensation of aldehyde (I) with methylamine using TiCl4 as the dehydrating reagent produced aldimine (III), which was then reduced to amine (IV) by means of NaBH4.

参考文献 中间体
合成目标
【1】 Zhou, Y.; Zhang, W.; Li, K.; Jiang, Y.; Li, Y.; Wang, X.; The synthesis and antifungal activity of the substituted naphthalenemethanamines. Chin Journal of Medicinal Chemistry 1999, 9, 7, 7.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
11021 Methanamine; Methylamine 74-89-5 CH5N 详情 详情
(I) 12314 1-Naphthaldehyde 66-77-3 C11H8O 详情 详情
(II) 35129 1-naphthylmethanol 4780-79-4 C11H10O 详情 详情
(III) 35130 N-[(Z)-1-naphthylmethylidene]methanamine; N-methyl-N-[(Z)-1-naphthylmethylidene]amine C12H11N 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

合成路线8

该中间体在本合成路线中的序号：(IV)

2,4-Dichlorobenzoic acid (V) was converted to acid chloride (VI) using SOCl2. Further Friedel-Crafts condensation of (VI) with toluene in the presence of AlCl3 produced benzophenone (VII). Benzylic bromination of (VII) with N-bromosuccinimide gave bromide (VIII). Finally, displacement of the bromine of (VIII) by means of amine (IV) furnished the title compound.

参考文献 中间体
合成目标
【1】 Zhou, Y.; Zhang, W.; Li, K.; Jiang, Y.; Li, Y.; Wang, X.; The synthesis and antifungal activity of the substituted naphthalenemethanamines. Chin Journal of Medicinal Chemistry 1999, 9, 7, 7.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(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
(V) 33443 2,4-dichlorobenzoic carboxylic acid; 2,4-dichlorobenzoic acid 50-84-0 C7H4Cl2O2 详情 详情
(VI) 35131 2,4-dichlorobenzoyl chloride; 2,4-Dichlorophenacylchloride 89-75-8 C7H3Cl3O 详情 详情
(VII) 35132 (2,4-dichlorophenyl)(4-methylphenyl)methanone C14H10Cl2O 详情 详情
(VIII) 35133 [4-(bromomethyl)phenyl](2,4-dichlorophenyl)methanone C14H9BrCl2O 详情 详情

合成路线9

该中间体在本合成路线中的序号：(VIII)

The title compound was prepared by solid-phase synthesis using a 2-chlorotrityl resin, chloride form. N2-(Benzyloxycarbonyl)-L-2,3-diaminopropionic acid (I) was protected as the Fmoc derivative (II) upon treatment with N-(Fmoc-oxy)succinimide. After attachment of the protected diaminoacid (II) to the chloride resin, the Fmoc group was selectively removed by means of piperidine in DMF to give the resin-bound Cbz-2,3-diaminopropionic acid (III). Acylation of the free amino function of (III) with 4-(chloromethyl)benzoyl chloride (IV) provided amide (V). The chloride group of (V) was then displaced with 2-(aminomethyl)benzimidazole (VI), yielding resin (VII). The required urea functionality (IX) was obtained by coupling (VII) with cyclohexyl isocyanate (VIII). Finally, cleavage of the carboxylic acid from the resin (IX) was achieved by treatment with trifluoroacetic acid in moist dichloromethane.

参考文献 中间体
合成目标
【1】 Neustadt, B.R.; Smith, E.M. (Schering Corp.); Benzimidazole cpds. that are vitronectin receptor antagonists. EP 1135374; WO 0032578 .
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),(III) 18008 (2S)-3-amino-2-[[(benzyloxy)carbonyl]amino]propionic acid; N(alpha)-Z-L-2,3-diaminopropionic acid 35761-26-3 C11H14N2O4 详情 详情
(II) 49111 (2S)-2-[[(benzyloxy)carbonyl]amino]-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propionic acid C26H24N2O6 详情 详情
(IV) 49112 4-(Chloromethyl)benzoyl chloride; p-(Chloromethyl)benzoyl chloride 876-08-4 C8H6Cl2O 详情 详情
(V) 49113 (2S)-2-[[(benzyloxy)carbonyl]amino]-3-[[4-(chloromethyl)benzoyl]amino]propionic acid C19H19ClN2O5 详情 详情
(VI) 49114 1H-benzimidazol-2-ylmethylamine; 1H-benzimidazol-2-ylmethanamine C8H9N3 详情 详情
(VII) 49115 (2S)-3-[(4-[[(1H-benzimidazol-2-ylmethyl)amino]methyl]benzoyl)amino]-2-[[(benzyloxy)carbonyl]amino]propionic acid C27H27N5O5 详情 详情
(VIII) 10108 N-Methyl(1-naphthyl)methanamine; N-Methyl-N-(1-naphthylmethyl)amine; 1-Methyl-1-naphthalenemethylamine 65473-13-4 C12H13N 详情 详情
(IX) 49116 (2S)-3-[[4-([(1H-benzimidazol-2-ylmethyl)[(cyclohexylamino)carbonyl]amino]methyl)benzoyl]amino]-2-[[(benzyloxy)carbonyl]amino]propionic acid C34H38N6O6 详情 详情
Extended Information