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【结 构 式】

【分子编号】22239

【品名】6-methyl-2,4-bis(methylsulfanyl)-3-pyridinylamine; 6-methyl-2,4-bis(methylsulfanyl)-3-pyridinamine

【CA登记号】

【 分 子 式 】C8H12N2S2

【 分 子 量 】200.32876

【元素组成】C 47.97% H 6.04% N 13.98% S 32.01%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(III)

The reaction of 2,2-difluoro-2-(4-isobutylphenyl)acetic acid (I) with oxalyl chloride in dichloromethane gives the corresponding acyl chloride (II), which is then treated with 6-methyl-2,4-bis(methylsulfanyl)pyridine-3-amine (III) and 4-(dimethylamino)pyridine (DMAP) in the same solvent.

1 Ko, S.S.; Wilde, R.G.; DeLucca, I.; Li, H.-Y.; Kezar, H.S. III; Boswell, G.A.; Srivastava, A.S. (DuPont Pharmaceuticals Co.); Amides for the treatment of atherosclerosis. US 5583147 .
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) 27008 2,2-difluoro-2-(4-isobutylphenyl)acetic acid C12H14F2O2 详情 详情
(II) 27009 2,2-difluoro-2-(4-isobutylphenyl)acetyl chloride C12H13ClF2O 详情 详情
(III) 22239 6-methyl-2,4-bis(methylsulfanyl)-3-pyridinylamine; 6-methyl-2,4-bis(methylsulfanyl)-3-pyridinamine C8H12N2S2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VI)

Condensation of 4-bromobenzaldehyde (I) with 4-fluorophenol (II) in the presence of K2CO3 in refluxing dimethylacetamide gave ether (III). Subsequent reductive amination of (III) with cycloheptylamine (IV) using ethanolic NaBH4 afforded secondary amine (V). Phenyl carbamate (VIII) was obtained by treatment of aminopyridine (VI) with phenyl chloroformate (VII) and dimethylaniline. Condensation of this carbamate with amine (V) in the presence of Et3N in refluxing toluene furnished urea (IX) (1). Both sulfide groups of (IX) were finally oxidized to sulfone using meta-chloroperbenzoic acid in CH2Cl2.

1 Tanaka, A.; Terasawa, T.; Hagihara, H.; Ishibe, N.; Sawada, M.; Sakuma, Y.; Hashimoto, M.; Takasugi, H.; Tanaka, H.; Inhibitors of acyl-CoA:cholesterol O-acyltransferase. 3. Discovery of a novel series of N-alkyl-N-[(fluorophenoxy)benzyl]-N'-arylureas with weak toxicological effects on adrenal glands. J Med Chem 1998, 41, 22, 4408.
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) 22231 4-Bromobenzaldehyde 1122-91-4 C7H5BrO 详情 详情
(II) 19639 4-fluorophenol 371-41-5 C6H5FO 详情 详情
(III) 22233 4-(4-fluorophenoxy)benzaldehyde C13H9FO2 详情 详情
(IV) 22234 cycloheptanamine; cycloheptylamine 5452-35-7 C7H15N 详情 详情
(VI) 22235 N-cycloheptyl-N-[4-(4-fluorophenoxy)benzyl]amine; N-[4-(4-fluorophenoxy)benzyl]cycloheptanamine C20H24FNO 详情 详情
(VI) 22239 6-methyl-2,4-bis(methylsulfanyl)-3-pyridinylamine; 6-methyl-2,4-bis(methylsulfanyl)-3-pyridinamine C8H12N2S2 详情 详情
(VII) 13580 1-[(Chlorocarbonyl)oxy]benzene; phenyl chloroformate 1885-14-9 C7H5ClO2 详情 详情
(VIII) 18000 phenyl 6-methyl-2,4-bis(methylsulfanyl)-3-pyridinylcarbamate C15H16N2O2S2 详情 详情
(IX) 22241 N-cycloheptyl-N-[4-(4-fluorophenoxy)benzyl]-N'-[6-methyl-2,4-bis(methylsulfanyl)-3-pyridinyl]urea C29H34FN3O2S2 详情 详情
Extended Information