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【结 构 式】

【分子编号】41424

【品名】1,4-dioxaspiro[4.5]decan-8-one oxime

【CA登记号】

【 分 子 式 】C8H13NO3

【 分 子 量 】171.19616

【元素组成】C 56.13% H 7.65% N 8.18% O 28.04%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XI)

Condensation of pyruvic aldehyde dimethyl acetal (V) with dimethylformamide dimethyl acetal produced enamino ketone (VI). Cyclization of (VI) with thiourea (VII), followed by methylation with iodomethane furnished the (methylsulfanyl)pyrimidine (VIII). Acid hydrolysis of the dimethyl acetal gave rise to aldehyde (IX). Cyclohexanedione monoketal (X) was converted to oxime (XI) and then hydrogenated to give amine (XII). This was condensed with aldehyde (IX) yielding imine (XIII). Reaction of imine (XIII) with sulfonyl isocyanide (IV) gave rise to imidazole (XIV). The methylsulfanyl group of (XIV) was then oxidized to sulfone (XV) employing oxone®. Further displacement of the methylsulfonyl group of (XV) with NaOMe produced the methoxy pyrimidine (XVI). After ketal (XVI) hydrolysis, reduction of the resulting ketone (XVII) with NaBH4 furnished the title alcohol.

1 Adams, J.L.; Garigipati, R.S.; Sorenson, M.E. (SmithKline Beecham plc); Novel cycloalkyl substd. imidazoles. EP 0889726; JP 2000503304; WO 9725048 .
2 Adams, J.L.; Garigipati, R.S. (SmithKline Beecham plc); Novel cycloalkyl substd. imidazoles. EP 0883402; WO 9725047 .
3 Boehm, J.C.; Garigipati, R.S.; Adams, J.L. (SmithKline Beecham Corp.); Novel cycloalkyl substd. imidazoles. EP 1019396; WO 9901452 .
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) 25595 4-Fluoro-alpha-(4-methylphenylsulfonyl)benzyl isocyanide C15H12FNO2S 详情 详情
(V) 25433 1,1-dimethoxyacetone 6342-56-9 C5H10O3 详情 详情
(VI) 25434 (E)-4-(dimethylamino)-1,1-dimethoxy-3-buten-2-one C8H15NO3 详情 详情
(VII) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(VIII) 41422 methoxy[2-(methylsulfanyl)-4-pyrimidinyl]methyl methyl ether; 4-(dimethoxymethyl)-2-(methylsulfanyl)pyrimidine C8H12N2O2S 详情 详情
(IX) 41423 2-(methylsulfanyl)-4-pyrimidinecarbaldehyde C6H6N2OS 详情 详情
(X) 11377 1,4-Dioxaspiro[4.5]decan-8-one 4746-97-8 C8H12O3 详情 详情
(XI) 41424 1,4-dioxaspiro[4.5]decan-8-one oxime C8H13NO3 详情 详情
(XII) 41425 1,4-dioxaspiro[4.5]dec-8-ylamine; 1,4-dioxaspiro[4.5]decan-8-amine C8H15NO2 详情 详情
(XIII) 41426 N-(1,4-dioxaspiro[4.5]dec-8-yl)-N-[(Z)-[2-(methylsulfanyl)-4-pyrimidinyl]methylidene]amine; N-[(Z)-[2-(methylsulfanyl)-4-pyrimidinyl]methylidene]-1,4-dioxaspiro[4.5]decan-8-amine C14H19N3O2S 详情 详情
(XIV) 41427 4-[1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-(4-fluorophenyl)-1H-imidazol-5-yl]-2-(methylsulfanyl)pyrimidine; 4-[1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-(4-fluorophenyl)-1H-imidazol-5-yl]-2-pyrimidinyl methyl sulfide C22H23FN4O2S 详情 详情
(XV) 41428 4-[1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-(4-fluorophenyl)-1H-imidazol-5-yl]-2-(methylsulfonyl)pyrimidine; 4-[1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-(4-fluorophenyl)-1H-imidazol-5-yl]-2-pyrimidinyl methyl sulfone C22H23FN4O4S 详情 详情
(XVI) 41429 4-[1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-(4-fluorophenyl)-1H-imidazol-5-yl]-2-pyrimidinyl methyl ether; 4-[1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-(4-fluorophenyl)-1H-imidazol-5-yl]-2-methoxypyrimidine C22H23FN4O3 详情 详情
(XVII) 41430 4-[4-(4-fluorophenyl)-5-(2-methoxy-4-pyrimidinyl)-1H-imidazol-1-yl]cyclohexanone C20H19FN4O2 详情 详情
Extended Information