2-({4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl}amino)-1-ethanol -Drug Synthesis Database

【结构式】

【分子编号】63166

【品名】2-({4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl}amino)-1-ethanol

【CA登记号】

【分子式】C₁₉H₁₉FN₈O

【分子量】394.4115832

【元素组成】C 57.86% H 4.86% F 4.82% N 28.41% O 4.06%

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：(VII)

The cyclization of 1-(2-fluorobenzyl)pyrazolo[3,4-b]pyridine-3-carboxamidine (I) (see scheme no. 28591301a, intermediate (IX)) with phenylazomalononitrile (II) by means of NaOMe in hot DMF gives the pyrimidine (III), which is reduced with H2 over RaNi in hot DMF to yield the triaminopyrimidine (IV). The reductocondensation of (IV) with 2-(tert-butyldimethylsilyloxy)acetaldehyde (V) by means of NaBH3CN in methanol/AcOH affords the adduct (VI), which is desilylated by means of TBAF in THF to provide the 2-hydroxyethylamino derivative (VII). Finally, this compound is cyclized with aqueous glyoxal (VIII) to furnish the target tricyclic compound.

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】 Kern, A.; Stasch, J.-P.; Straub, A.; Dembowsky, K.; Alonso-Alija, C. (Bayer AG); Substd. pyrazole deriv.. DE 10021069; WO 0183490 .

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)	63162	2-[(E)-2-phenyldiazenyl]malononitrile	6017-21-6	C₉H₆N₄	详情	详情
(III)	63163	2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-[(E)-2-phenyldiazenyl]-4,6-pyrimidinediamine; 6-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-[(E)-2-phenyldiazenyl]-4-pyrimidinylamine	428854-23-3	C₂₃H₁₈FN₉	详情	详情
(IV)	63164	4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinylamine; 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4,5,6-pyrimidinetriamine	428854-24-4	C₁₇H₁₅FN₈	详情	详情
(V)	61170	2-{[tert-butyl(dimethyl)silyl]oxy}acetaldehyde；tert-butyldimethylsilyloxy acetaldehyde	102191-92-4	C₈H₁₈O₂Si	详情	详情
(VI)	63165	N~5~-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4,5,6-pyrimidinetriamine; 6-amino-5-[(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-pyrimidinylamine		C₂₅H₃₃FN₈OSi	详情	详情
(VII)	63166	2-({4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl}amino)-1-ethanol		C₁₉H₁₉FN₈O	详情	详情
(VIII)	32557	glyoxal; 2-oxoacetaldehyde	107-22-2	C₂H₂O₂	详情	详情

Extended Information