6-(3-[[1-(4-bromo-2-methylphenyl)-1H-imidazol-2-yl]sulfanyl]propoxy)-3,4-dihydro-2(1H)-quinolinone -Drug Synthesis Database

【结构式】

【分子编号】30237

【品名】6-(3-[[1-(4-bromo-2-methylphenyl)-1H-imidazol-2-yl]sulfanyl]propoxy)-3,4-dihydro-2(1H)-quinolinone

【CA登记号】

【分子式】C₂₂H₂₂BrN₃O₂S

【分子量】472.4057

【元素组成】C 55.94% H 4.69% Br 16.91% N 8.89% O 6.77% S 6.79%

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：(XV)

In a further procedure, the bromophenyl imidazole (XIII) was prepared by treatment of 4-bromo-2-methylaniline (IX) with carbon disulfide and DCC to produce isothiocyanate (X). Condensation with 2,2-diethoxyethylamine (XI) gave thiourea (XII), which was cyclized in refluxing 8 N HCl to the 1-aryl-2-mercaptoimidazole (XIII). This was alkylated with the chloropropoxy quinolinone (XIV) to give sulfide (XV). Sharpless oxidation in the presence of D-diethyl tartrate produced the (S)-sulfoxide (XVI). Finally, hydrogenolysis of the halogen atom over Pd/C furnished the title compound.

参考文献中间体

合成目标

【1】 Nishi, T.; Uno, T.; Shu, Y.; Tamura, K.; Okada, M. (Otsuka Pharmaceutical Co., Ltd.); Carbostyril derivs.. EP 0651747; JP 1995033765; US 5541198; WO 9426732 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IX)	30231	4-bromo-2-methylphenylamine; 4-bromo-2-methylaniline	583-75-5	C₇H₈BrN	详情	详情
(X)	30232	4-bromo-2-methylphenyl isothiocyanate; 4-bromo-1-isothiocyanato-2-methylbenzene	19241-38-4	C₈H₆BrNS	详情	详情
(XI)	30233	3,3-diethoxypropylamine; 3,3-diethoxy-1-propanamine	41365-75-7	C₇H₁₇NO₂	详情	详情
(XII)	30234	N-(4-bromo-2-methylphenyl)-N'-(3,3-diethoxypropyl)thiourea		C₁₅H₂₃BrN₂O₂S	详情	详情
(XIII)	30235	1-(4-bromo-2-methylphenyl)-1H-imidazol-2-ylhydrosulfide; 1-(4-bromo-2-methylphenyl)-1H-imidazole-2-thiol		C₁₀H₉BrN₂S	详情	详情
(XIV)	30236	6-(3-chloropropoxy)-3,4-dihydro-2(1H)-quinolinone		C₁₂H₁₄ClNO₂	详情	详情
(XV)	30237	6-(3-[[1-(4-bromo-2-methylphenyl)-1H-imidazol-2-yl]sulfanyl]propoxy)-3,4-dihydro-2(1H)-quinolinone		C₂₂H₂₂BrN₃O₂S	详情	详情
(XVI)	30238	6-(3-[[1-(4-bromo-2-methylphenyl)-1H-imidazol-2-yl]sulfinyl]propoxy)-3,4-dihydro-2(1H)-quinolinone		C₂₂H₂₂BrN₃O₃S	详情	详情

Extended Information