11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one -Drug Synthesis Database

【结构式】

【分子编号】10435

【品名】11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one

【CA登记号】

【分子式】C₁₇H₁₂ClNO₂

【分子量】297.74052

【元素组成】C 68.58% H 4.06% Cl 11.91% N 4.7% O 10.75%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XXI)

7) [12b-14C]-Org-5222: The condensation of labeled sarcosine methyl ester (XVI) (prepared from sarcosine (XV) with SOCl2 and methanol) with 2-(5-chloro-2-phenoxyphenyl)acetyl chloride (XVIII) (prepared from the corresponding acid (XVII) and SOCl2) yields the acylated sarcosine (XIX), which is cyclized by means of potassium tert-butoxide in toluene to the pyrrolidinedione (XX). A further cyclization of (XX) with polyphosphoric acid affords [3a-14C]-11-chloro-2-methyl-2,3-dihydro-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (XXI), which is reduced with Mg in methanol to the trans-isomeric amide (XXII) (along with the cis-isomer, which is separated by HPLC). Finally, the amide (XXII) is reduced with LiAlH4/AlCl3 in ethyl ether.

参考文献中间体

合成目标

【1】 Wagenaars, G.; Vader, J.; Sperling, E.; Terpstra, A.; Kaspersen, F.; Hilberink, P.; Schlachter, I.; The syntheses of radiolabelled Org 5222 and its main metabolite Org 30526. J Label Compd Radiopharm 1994, 34, 9, 845.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XXIIa)	10436	(3aS,12bS)-11-Chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one		C₁₇H₁₄ClNO₂	详情	详情
(XXIIb)	44653	(3aS,12bR)-11-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one		C₁₇H₁₄ClNO₂	详情	详情
(XXIIa)	44659	(3aS,12bS)-11-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one		C₁₇H₁₄ClNO₂	详情	详情
(XXIIb)	44660	(3aS,12bR)-11-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one		C₁₇H₁₄ClNO₂	详情	详情
(XV)	10429	N-Methylglycine; Sarcosine; 2-(Methylamino)acetic acid	107-97-1	C₃H₇NO₂	详情	详情
(XV)	44654	2-(methylamino)acetic acid		C₃H₇NO₂	详情	详情
(XVI)	10430	methyl 2-(methylamino)acetate; methyl N-methylglycinate	5473-12-1	C₄H₉NO₂	详情	详情
(XVI)	44655	methyl 2-(methylamino)acetate		C₄H₉NO₂	详情	详情
(XVII)	10431	2-(5-Chloro-2-phenoxyphenyl)acetic acid		C₁₄H₁₁ClO₃	详情	详情
(XVIII)	10432	2-(5-Chloro-2-phenoxyphenyl)acetyl chloride		C₁₄H₁₀Cl₂O₂	详情	详情
(XIX)	10433	methyl 2-[[2-(5-chloro-2-phenoxyphenyl)acetyl](methyl)amino]acetate		C₁₈H₁₈ClNO₄	详情	详情
(XIX)	44656	methyl 2-[[2-(5-chloro-2-phenoxyphenyl)acetyl](methyl)amino]acetate		C₁₈H₁₈ClNO₄	详情	详情
(XX)	10434	3-(5-Chloro-2-phenoxyphenyl)-1-methyl-2,4-pyrrolidinedione		C₁₇H₁₄ClNO₃	详情	详情
(XX)	44657	3-(5-chloro-2-phenoxyphenyl)-1-methyl-2,4-pyrrolidinedione		C₁₇H₁₄ClNO₃	详情	详情
(XXI)	10435	11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one		C₁₇H₁₂ClNO₂	详情	详情
(XXI)	44658	11-chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one		C₁₇H₁₂ClNO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

参考文献中间体

合成目标

【1】 Van der Linden M, Roeters T, Harting R, et al. 2008. Debottlenecking the synthesis route of asenapine. Organic Process Reasearch & Development, 12: 196.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	10435	11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one	C₁₇H₁₂ClNO₂	详情	详情
(II)	10436	(3aS,12bS)-11-Chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one	C₁₇H₁₄ClNO₂	详情	详情
(III)	44653	(3aS,12bR)-11-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one	C₁₇H₁₄ClNO₂	详情	详情
(IV)	67046	(10R,11R)-8-chloro-11-((methylamino)methyl)-10,11-dihydrodibenzo[b,f]oxepine-10-carboxylic acid hydrochloride	C₁₇H₁₆ClNO₃.HCl	详情	详情

Extended Information