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【结 构 式】 
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【分子编号】44790 【品名】tert-butyl 2-[3-[[(2-iodobenzyl)sulfonyl]amino]-6-methyl-2-oxo-1(2H)-pyridinyl]acetate 【CA登记号】 |
【 分 子 式 】C19H23IN2O5S 【 分 子 量 】518.37257 【元素组成】C 44.02% H 4.47% I 24.48% N 5.4% O 15.43% S 6.19% |
合成路线1
该中间体在本合成路线中的序号：(XVI)Synthesis of intermediate (VI): Treatment of pyridone (X) with diphenyl phosphoryl azide (DPPA) followed by reaction with benzyl alcohol affords the protected derivative (XI), which then reacts with tert-butyl bromoacetate (XII) by means of Cs2CO3 to provide the acetate derivative (XIII). Hydrogenation of (XIII) over Pd/C allows Cbz removal, giving amine (XIV), which is then condensed with iodo derivative (XV) to furnish sulfonamide compound (XVI). Finally, hydrolysis of (XVI) is achieved by treatment with TFA to afford the target intermediate (VI).
| 【1】 Soll, R.M.; Lu, T.; Tomczuk, B.E.; Spurlino, J.; Pan, W.; Bone, R.; Green, D.W.; Heteroaryl keto thrombin inhibitors: Design and synthesis. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 285. |
| 【2】 Tumczuk, B.E.; Pan, W.; Soll, R.M.; Lu, T. (3-Dimensional Pharmaceuticals, Inc.); Heteroaryl protease inhibitors and diagnostic imaging agents. WO 0104117 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 44786 | 2-[3-[[(2-iodobenzyl)sulfonyl]amino]-6-methyl-2-oxo-1(2H)-pyridinyl]acetic acid | C15H15IN2O5S | 详情 | 详情 | |
| (X) | 44789 | 6-methyl-2-oxo-1,2-dihydro-3-pyridinecarboxylic acid | C7H7NO3 | 详情 | 详情 | |
| (XI) | 26603 | benzyl 6-methyl-2-oxo-1,2-dihydro-3-pyridinylcarbamate | C14H14N2O3 | 详情 | 详情 | |
| (XII) | 17430 | 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate | 5292-43-3 | C6H11BrO2 | 详情 | 详情 |
| (XIII) | 26604 | tert-butyl 2-[3-[[(benzyloxy)carbonyl]amino]-6-methyl-2-oxo-1(2H)-pyridinyl]acetate | C20H24N2O5 | 详情 | 详情 | |
| (XIV) | 26605 | tert-butyl 2-[3-amino-6-methyl-2-oxo-1(2H)-pyridinyl]acetate | C12H18N2O3 | 详情 | 详情 | |
| (XV) | 44791 | (2-iodophenyl)methanesulfonyl chloride | C7H6ClIO2S | 详情 | 详情 | |
| (XVI) | 44790 | tert-butyl 2-[3-[[(2-iodobenzyl)sulfonyl]amino]-6-methyl-2-oxo-1(2H)-pyridinyl]acetate | C19H23IN2O5S | 详情 | 详情 |