ethyl (3aS,12bS)-5-chloro-1,3,3a,12b-tetrahydro-2H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】10426

【品名】ethyl (3aS,12bS)-5-chloro-1,3,3a,12b-tetrahydro-2H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole-2-carboxylate

【CA登记号】

【分子式】C₁₉H₁₈ClNO₃

【分子量】343.80956

【元素组成】C 66.38% H 5.28% Cl 10.31% N 4.07% O 13.96%

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：(XI)

3) [11-3H]-Org-5222: The iodination of Org-5222 (VI) with N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid in CH2Cl2 gives the 11-iodo derivative (VII), which is then reduced with 3H2 and Pd/C in ethanol. 4) [7,11-3H2]-Org-5222: The nitration of Org-5222 (VI) with HNO3/H2SO4 gives the 7,11-dinitro derivative (VIII), which is reduced with Fe/acetic acid to the 7,11-diamino compound (IX). The reaction of (IX) with NaNO2/HCl in the presence of KI yields the 7,11-diiodo derivative (X), which is then reduced with 3H2 and Pd/C in ethanol as before. 5) [7,11-3H2]-Org-30526: The reaction of [7,11-3H2]- Org-5222 with ethyl chloroformate in refluxing toluene gives the carbamate (XI), which is then hydrolyzed under strongly basic conditions.

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	分子式	供应商	用于合成
(VI)	10420	(3aS,12bS)-5-Chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole	C₁₇H₁₆ClNO	详情	详情
(VII)	10421	(3aS,12bS)-5-Chloro-11-iodo-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole	C₁₇H₁₅ClINO	详情	详情
(VIII)	10422	(3aS,12bS)-5-Chloro-2-methyl-7,11-dinitro-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole	C₁₇H₁₄ClN₃O₅	详情	详情
(IX)	10423	(3aS,12bS)-11-Chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole-5,9-diamine; (3aS,12bS)-11-Amino-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-7-ylamine	C₁₇H₁₈ClN₃O	详情	详情
(X)	10424	(3aS,12bS)-5-Chloro-7,11-diiodo-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole	C₁₇H₁₄ClI₂NO	详情	详情
(XI)	10426	ethyl (3aS,12bS)-5-chloro-1,3,3a,12b-tetrahydro-2H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole-2-carboxylate	C₁₉H₁₈ClNO₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XII)

6) [11-3H]-Org-30526: The reaction of Org-5222 (VI) with ethyl chloroformate in refluxing toluene gives the carbamate ester (XII), which is hydrolyzed with HBr to afford Org-30526 (XIII). The iodination of (XIII) with NIS and trifluoromethanesulfonic acid yields the 11-iodo derivative (XIV), which is finally reduced with 3H2 and Pd/C in ethanol.

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	分子式	供应商	用于合成
(VI)	10420	(3aS,12bS)-5-Chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole	C₁₇H₁₆ClNO	详情	详情
(XII)	10426	ethyl (3aS,12bS)-5-chloro-1,3,3a,12b-tetrahydro-2H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole-2-carboxylate	C₁₉H₁₈ClNO₃	详情	详情
(XIII)	10427	(3aS,12bS)-5-Chloro-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole	C₁₆H₁₄ClNO	详情	详情
(XIV)	10428	(3aS,12bS)-5-Chloro-11-iodo-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole	C₁₆H₁₃ClINO	详情	详情

Extended Information