2-oxocycloheptanecarbaldehyde -Drug Synthesis Database

【结构式】

【分子编号】45624

【品名】2-oxocycloheptanecarbaldehyde

【CA登记号】641-70-3

【分子式】C₈H₁₂O₂

【分子量】140.18208

【元素组成】C 68.55% H 8.63% O 22.83%

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：(I)

Condensation of 2-formylcycloheptanone (I) with ethyl 3-aminocrotonate (II) provides ethyl carboxylate (III), which is then converted into carbonylguanidine (VI) by reaction with free guanidine (V) (obtained from guanidine hydrochloride (IV) by treatment with Na/MeOH) in refluxing isopropanol. Alternatively, carbonylguanidine (VI) can also be obtained by saponification of ethyl ester (III) with refluxing NaOH to yield carboxylic acid (VII), which is then activated with oxalyl chloride (A) in CH2Cl2 or with CDI in THF to allow condensation with guanidine (V) in THF. Finally, the corresponding maleate can be obtained by reaction of carbonylguanidine (VI) with maleic acid (VIII) in MeOH.

参考文献中间体

合成目标

【1】 Kogi, K.; Takahashi, A.; Gengyou, K.; Aihara, K.; Yoneyama, F.; Sasamori, J.; Yoneyama, S.; Satoh, T.; Yamada, S.; Kimura, T. (Toa Eiyo Ltd.); Cycloalka[b]pyridine-3-carbonylguanidine derivs., process for producing the same, and drugs containing the same. EP 0972767; WO 9839300 .

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),(V)	14790	Guanidine	113-00-8	CH₅N₃	详情	详情
(A)	29841	Oxalyl chloride; 2-Chloro-2-oxoacetyl chloride	79-37-8	C₂Cl₂O₂	详情	详情
(I)	45624	2-oxocycloheptanecarbaldehyde	641-70-3	C₈H₁₂O₂	详情	详情
(II)	45628	Ethyl (Z)-3-amino-2-butenoate; 3-amino-2-butenoic acid ethyl ester; Ethyl 3-aminocrotonate; 3-Aminocrotonic acid ethyl ester	626-34-6	C₆H₁₁NO₂	详情	详情
(III)	45625	ethyl 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate		C₁₄H₁₉NO₂	详情	详情
(VI)	45626	N-[(2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-3-yl)carbonyl]guanidine		C₁₃H₁₈N₄O	详情	详情
(VII)	45627	2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylic acid		C₁₂H₁₅NO₂	详情	详情
(VIII)	37495	Maleic acid; (Z)-2-Butenedioic acid	110-16-7	C₄H₄O₄	详情	详情

Extended Information