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【结 构 式】

【分子编号】58783

【品名】6-(tert-butyl) 3-ethyl 2-[(2-ethoxy-2-oxoacetyl)amino]-4,7-dihydrothieno[2,3-c]pyridine-3,6(5H)-dicarboxylate

【CA登记号】

【 分 子 式 】C19H26N2O7S

【 分 子 量 】426.49072

【元素组成】C 53.51% H 6.14% N 6.57% O 26.26% S 7.52%

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:(VI)

Knoevenagel condensation between N-Boc-4-piperidinone (I) and ethyl cyanoacetate (II) produced the piperidinylidene cyanoacetate (III), which was further converted to the thienopyridine derivative (IV) upon treatment with sulfur and morpholine. Acylation of amine (IV) with ethyl oxalyl chloride (V) furnished the oxalamide (VI). Subsequent hydrolysis of the ester groups of (VI) under basic conditions led to diacid (VII). The title compound was finally obtained by trifluoroacetic acid-promoted Boc group cleavage.

1 Modulators of protein tyrosine phosphatases. WO 9946237 .
2 Jones, T.K.; Ripka, W.C.; Andersen, H.S.; Olsen, O.H.; Bakir, F.; Branner, S.; Iversen, L.F.; Holsworth, D.D.; Axe, F.U.; Ge, Y.; Uyeda, R.T.; Judge, L.M.; Moeller, N.P.H. (Novo Nordisk A/S; Ontogen Corp.); Modulators of protein tyrosine phosphatases (PTPases). JP 2002506072; US 6410586; WO 9946267 .
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) 18620 tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone 79099-07-3 C10H17NO3 详情 详情
(II) 11877 Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate 105-56-6 C5H7NO2 详情 详情
(III) 58781 tert-butyl 4-(1-cyano-2-ethoxy-2-oxoethylidene)-1-piperidinecarboxylate C15H22N2O4 详情 详情
(IV) 58782 6-(tert-butyl) 3-ethyl 2-amino-4,7-dihydrothieno[2,3-c]pyridine-3,6(5H)-dicarboxylate C15H22N2O4S 详情 详情
(V) 11043 Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride 4755-77-5 C4H5ClO3 详情 详情
(VI) 58783 6-(tert-butyl) 3-ethyl 2-[(2-ethoxy-2-oxoacetyl)amino]-4,7-dihydrothieno[2,3-c]pyridine-3,6(5H)-dicarboxylate C19H26N2O7S 详情 详情
(VII) 58784 6-(tert-butoxycarbonyl)-2-[(carboxycarbonyl)amino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid C15H18N2O7S 详情 详情
Extended Information