ethyl 4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】63161

【品名】ethyl 4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinecarboxylate

【CA登记号】

【分子式】C₂₀H₁₇FN₆O₂

【分子量】392.3926232

【元素组成】C 61.22% H 4.37% F 4.84% N 21.42% O 8.15%

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：(III)

The cyclization of 1-(2-fluorobenzyl)pyrazolo[3,4-b]pyridine-3-carboxamidine (I) (see scheme no. 28591301a, intermediate (IX)) with ethyl 2-(ethoxymethylene)cyanacetate (II) in refluxing toluene gives the pyrimidine-5-carboxylate derivative (III), which is cyclized to the target 1-hydroxycyclopropyl derivation by reaction with CH2I2 and SmI2 in hot THF.

参考文献中间体

合成目标

【1】 Straub, A.; Benet-Buckholz, J.; Fröde, R.; Kern, A.; Kohlsdorfer, C.; Schmitt, P.; Schwarz, T.; Siefert, H.-M.; Stasch, J.-P.; Metabolites of orally active NO-independent pyrazolopyridine stimulators of soluble guanylate cyclase. Bioorg Med Chem 2002, 10, 6, 1711.
【2】 Perzborn, E.; Kern, A.; Stasch, J.-P.; Straub, A.; Feurer, A.; Dembowsky, K.; Alonso-Alija, C.; Stahl, E. (Bayer AG); Substd. pyrazole deriv.. DE 19920352; WO 0066582 .

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)	50477	1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide	256376-68-8	C₁₄H₁₂FN₅	详情	详情
(II)	43563	ethyl (E)-2-cyano-3-ethoxy-2-propenoate；(E)-ethyl 2-cyano-3-ethoxyacrylate	94-05-3	C₈H₁₁NO₃	详情	详情
(III)	63161	ethyl 4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinecarboxylate		C₂₀H₁₇FN₆O₂	详情	详情

Extended Information