9-(3-bromo-4-fluorophenyl)-3a-hydroxy-2,3,3a,5,6,7,9,9a-octahydro-1H-2H-thieno[3,2-b]quinoline-1,1,8(4H)-trione -Drug Synthesis Database

【结构式】

【分子编号】51551

【品名】9-(3-bromo-4-fluorophenyl)-3a-hydroxy-2,3,3a,5,6,7,9,9a-octahydro-1H-2H-thieno[3,2-b]quinoline-1,1,8(4H)-trione

【CA登记号】

【分子式】C₁₇H₁₇BrFNO₄S

【分子量】430.2947232

【元素组成】C 47.45% H 3.98% Br 18.57% F 4.42% N 3.26% O 14.87% S 7.45%

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：(IV)

The Hantzsch reaction between 3-oxotetrahydrothiophene-1,1-dioxide (I), 3-bromo-4-fluorobenzaldehyde (II) and 3-amino-2-cyclohexen-1-one (III) in refluxing EtOH yielded the hydroxy tetrahydropyridine derivative (IV). Dehydration of the cyclic hemiaminal function of (IV) was carried out in refluxing toluene to produce the racemic dihydropyridine, which was resolved into the individual enantiomers by chiral HPLC.

参考文献中间体

合成目标

【1】 Drizin, I.; et al.; Novel sulfonyldihydropyridine potassium channel openers with potential utility in the treatment of overactive bladder (OAB). 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 197.
【2】 Drizin, I.; Holladay, M.W.; Carroll, W.A.; Zhang, H.Q.; Sullivan, J.P. (Abbott Laboratories Inc.); Potassium channel openers. EP 1040097; US 6265417; WO 9931059 .

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)	51549	3-Oxosulfolane		C₄H₆O₃S	详情	详情
(II)	51550	3-Bromo-4-fluorobenzaldehyde	77771-02-9	C₇H₄BrFO	详情	详情
(III)	31475	3-amino-2-cyclohexen-1-one	5220-49-5	C₆H₉NO	详情	详情
(IV)	51551	9-(3-bromo-4-fluorophenyl)-3a-hydroxy-2,3,3a,5,6,7,9,9a-octahydro-1H-2H-thieno[3,2-b]quinoline-1,1,8(4H)-trione		C₁₇H₁₇BrFNO₄S	详情	详情

Extended Information