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【结 构 式】

【分子编号】30260

【品名】2-(5-benzoyl-2-[[(4-methylphenyl)sulfonyl]imino]-1-pyridinyl)acetamide

【CA登记号】

【 分 子 式 】C21H19N3O4S

【 分 子 量 】409.46568

【元素组成】C 61.6% H 4.68% N 10.26% O 15.63% S 7.83%

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:(V)

Friedel-Crafts acylation of benzene with 6-chloronicotinyl chloride (I) using AlCl3 afforded ketone (II). Subsequent displacement of the chlorine atom of (II) by means of ethanolic ammonia at 145 C in a pressure reactor led to the aminopyridine (III), which was converted to sulfonamide (IV) by means of tosyl chloride in pyridine. Alkylation of the pyridine N of (IV) with iodoacetamide gave (V), and further cyclization in the presence of trifluoroacetic anhydride produced the imidazopyridine (VI). Phosphonate (VIII) was prepared by treatment of triethyl phosphonoacetate (VII) with methylamine. Horner-Emmons condensation of this phosphonate with ketone (VI) yielded the E-propenamide (IX). Selective iodination of (IX) at position 3 using N-iodosuccinimide furnished iodide (X). This compound was first deprotonated with PhLi, then subjected to a halogen-metal exchange reaction with tert-butyllithium, and the resulting trianion was reacted with isopropyl isopropanethiolsulfonate to give sulfide (XI). Finally, smooth hydrolysis of the trifluoroacetamide group of (XI) employing MeOH-CH2Cl2 in the presence of silica gel provided the title compound.

1 Hamdouchi, C.; de Blas, J.; del Prado, M.; Gruber, J.; Heinz, B.A.; Vance, L.; 2-Amino-3-substituted-6-[(E)-1-phenyl-2-(N-methylcarbamoyl)vinyl]imidazo[1,2-a]pyridines as a novel class of inhibitors of human rhinovirus: Stereospecific synthesis and antiviral activity. J Med Chem 1999, 42, 1, 50.
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) 30256 6-chloronicotinoyl chloride 58757-38-3 C6H3Cl2NO 详情 详情
(II) 30257 (6-chloro-3-pyridinyl)(phenyl)methanone C12H8ClNO 详情 详情
(III) 30258 (6-amino-3-pyridinyl)(phenyl)methanone C12H10N2O 详情 详情
(IV) 30259 N-(5-benzoyl-2-pyridinyl)-4-methylbenzenesulfonamide C19H16N2O3S 详情 详情
(V) 30260 2-(5-benzoyl-2-[[(4-methylphenyl)sulfonyl]imino]-1-pyridinyl)acetamide C21H19N3O4S 详情 详情
(VI) 30261 N-(6-benzoylimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide C16H10F3N3O2 详情 详情
(VII) 10019 Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate 867-13-0 C8H17O5P 详情 详情
(VIII) 30262 diethyl 2-(methylamino)-2-oxoethylphosphonate C7H16NO4P 详情 详情
(IX) 30263 (E)-N-methyl-3-phenyl-3-[2-[(2,2,2-trifluoroacetyl)amino]imidazo[1,2-a]pyridin-6-yl]-2-propenamide C19H15F3N4O2 详情 详情
(X) 30264 (E)-3-[3-iodo-2-[(2,2,2-trifluoroacetyl)amino]imidazo[1,2-a]pyridin-6-yl]-N-methyl-3-phenyl-2-propenamide C19H14F3IN4O2 详情 详情
(XI) 30265 (E)-3-[3-(isopropylsulfanyl)-2-[(2,2,2-trifluoroacetyl)amino]imidazo[1,2-a]pyridin-6-yl]-N-methyl-3-phenyl-2-propenamide C22H21F3N4O2S 详情 详情
Extended Information