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【结 构 式】

【分子编号】45626

【品名】N-[(2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-3-yl)carbonyl]guanidine

【CA登记号】

【 分 子 式 】C13H18N4O

【 分 子 量 】246.31228

【元素组成】C 63.39% H 7.37% N 22.75% O 6.5%

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)

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.

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