• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】32803

【品名】3-ethoxy-4-(tert-pentylamino)-3-cyclobutene-1,2-dione

【CA登记号】

【 分 子 式 】C11H17NO3

【 分 子 量 】211.26092

【元素组成】C 62.54% H 8.11% N 6.63% O 22.72%

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)

A general synthetic route to a series of novel N-aryl and N-benzyl diaminocyclobutenedione derivatives and pertinent SAR data have been reported elsewhere. KCO-616 can be conveniently synthesized in two steps as shown in Scheme 26121401a. An ethanolic solution of 3,4-diethoxy-3-cyclobutene-1,2-dione (I) is allowed to react with tert-amylamine (II) at room temperature for a period of 24 h to give intermediate 3-(1,1-dimethylpropylamino)-4-ethoxy-3-cyclobutene-1,2-dione (III) in 90% isolated, purified yield. The condensation of this compound with 2,4-dichloro-6-methylbenzylamine (IV, recrystallized from boiling diethyl ether) in ethanol at room temperature for 24 h affords analytically pure 3-(2,4-dichloro-6-methylbenzylamino)-4-(1,1-dimethylpropylamino)-3-cyclobutene-1,2-dione (KCO-616) in 92% yield.

1 Butera, J.A.; et al.; Substituted N-aryl-1,2-diaminocyclobutene-3,4-diones. I. N-Cyanoguanidine bioisosteres possessing in vivo bladder selectivity. 214th ACS Natl Meet (Sept. 7-11, Las Vegas) 1997, Abst MEDI 044.
2 McFarlane, G.R.; Gundersen, E.G.; Elokdah, H.; et al.; Benzylamino analogs of 1,2-diaminocyclobutene-3,4-dione as novel KATP-channel openers targeted for treatment of urge urinary incontinence . 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 35.
3 Antane, M.M.; Butera, J.A.; Antane, S.A.; et al.; Design and SAR of novel potassium channel openers targeted for urge urinary incontinence. I. N-Cyanoguanidine bioisosteres possessing in vivo bladder selectivity. J Med Chem 2000, 43, 6, 1187-1202.
4 Butera, J.A.; Argentieri, T.M.; KCO-616. Drugs Fut 2000, 25, 3, 239.
5 Antane, M.M.; Argentieri, T.M.; Gilbert, A.M.; et al.; Desing and SAR of novel potassium channel openers targeted for urge urinary incontinence. 2. Selective and potent benzylamino cyclobutenediones. J Med Chem 2000, 43, 6, 1203.
6 Antane, M.M.; Herbst, D.R.; McFarlane, G.R.; Gundersen, E.G.; Hirth, B.H.; Quagliato, D.A.; Graceffa, R.F.; Butera, J.A.; Gilbert, A.M. (American Home Products Corp.); Substd. N-arylmethylamino derivs. of cyclobutene-3, 4-diones. US 5763474; US 5780505; WO 9802413 .
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) 30975 3,4-diethoxy-3-cyclobutene-1,2-dione 5231-87-8 C8H10O4 详情 详情
(II) 24439 2-methyl-2-butanamine 594-39-8 C5H13N 详情 详情
(III) 32803 3-ethoxy-4-(tert-pentylamino)-3-cyclobutene-1,2-dione C11H17NO3 详情 详情
(IV) 32804 2,4-dichloro-6-methylbenzylamine; (2,4-dichloro-6-methylphenyl)methanamine 175278-27-0 C8H9Cl2N 详情 详情
Extended Information