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【结 构 式】

【分子编号】65713

【品名】2,2-Diethoxy-N,N-dimethylethylamine; (Dimethylamino)acetaldehyde diethyl acetal

【CA登记号】3616-56-6

【 分 子 式 】C8H19NO2

【 分 子 量 】161.2444

【元素组成】C 59.59% H 11.88% N 8.69% O 19.84%

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)

Acylation of 6-amino-4-(3-chloro-4-fluorophenylamino)-7-[tetrahydrofuran-3(S)-yloxy]quinazoline (I) with the acid chloride generated from bromocrotonic acid (II) and oxalyl chloride leads to the bromocrotonamide (III), which is finally submitted to bromide displacement with dimethylamine (1). Scheme1.
In an alternative method, aminoquinazoline (I) is acylated with diethylphosphonoacetic acid (IV) by means of carbonyldiimidazole in THF to give the phosphonoacetamide (V), which is finally condensed with (dimethylamino)acetaldehyde diethyl acetal (VI) under basic conditions (2). Scheme 1.

1 Himmelsbach, F., Langkopf, E., Solca, F., Jung, B., Baum, A., Blech, S. (Boehringer Ingelheim Pharma GmbH & Co., KG). Quinazoline derivatives, medicaments containing said compounds, their utilization and method for the production thereof. DE 10063435, EP 1345910, JP 2004516283, US 2002173509, US 2006100223, US 7019012, WO 0250043.
2 Soyka, R., Rall, W., Kulinna, C., Sieger, P., Schnaubelt, J. (Boehringer Ingelheim Pharma GmbH & Co., KG). Process for preparing amino crotonyl compounds. DE 10349113, EP 1678165, JP 2007510624, US 2005085495, WO 2005037824.
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) 65710 N4-(3-Chloro-4-fluorophenyl)-7-[[(3S)-tetrahydro-3-furanyl]oxy]-4,6-quinazolinediamine 314771-76-1 C18H16ClFN4O2 详情 详情
(II) 50563 (E)-4-bromo-2-butenoic acid 13991-36-1 C4H5BrO2 详情 详情
(III) 65711     C22H19BrClFN4O3 详情 详情
(IV) 36512 2-(diethoxyphosphoryl)acetic acid 3095-95-2 C6H13O5P 详情 详情
(V) 65712     C24H27ClFN4O6 详情 详情
(VI) 65713 2,2-Diethoxy-N,N-dimethylethylamine; (Dimethylamino)acetaldehyde diethyl acetal 3616-56-6 C8H19NO2 详情 详情
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