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【结 构 式】 
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【分子编号】64717 【品名】ethyl 2-[3-amino-4-{[(cyclopropylmethyl)amino]sulfonyl}-6-methyl-2-oxo-1(2H)-pyridinyl]acetate 【CA登记号】 |
【 分 子 式 】C14H21N3O5S 【 分 子 量 】343.40396 【元素组成】C 48.97% H 6.16% N 12.24% O 23.3% S 9.34% |
合成路线1
该中间体在本合成路线中的序号：(XIII)The acid chloride (X) is condensed with cyclopropylmethylamine (XI) to produce the sulfonamide (XII). Subsequent acidic Boc group cleavage in (XII) leads to the amine (XIII). Alkaline hydrolysis of the ethyl ester group of (XIII) provides the acid (XIV), which is subsequently coupled to 6-amino-3-(aminomethyl)-2-methylpyridine (XV) by means of EDC/HOAt to yield the amide (XVI). Finally, condensation of (XVI) with HCHO, followed by cyclization either in the presence of EDC or under acidic conditions, furnishes the target pyridothiadiazine. (1,2)
| 【1】 Sanderson, P.E.J.; Cutrona, K.J.; Savage, K.L.; Naylor-Olsen, A.M.; Bickel, D.J.; Bohn, D.L.; Clayton, F.C.; Krueger, J.A.; Lewis, S.D.; Lucas, B.J.; Lyle, E.A.; Wallace, A.A.; Welsh, D.C.; Yan, Y.; 3-Amino-4-sulfonylpyridinone acetamide and related pyridothiadiazine thrombin inhibitors. Bioorg Med Chem Lett 2003, 13, 8, 1441. |
| 【2】 Sanderson, P.E.; Cutrona, K. (Merck & Co., Inc.); Thrombin inhibitors. EP 1117660; JP 2002525370; US 6117888; WO 0018762 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 64715 | ethyl 2-[3-[bis(tert-butoxycarbonyl)amino]-4-(chlorosulfonyl)-6-methyl-2-oxo-1(2H)-pyridinyl]acetate | C20H29ClN2O9S | 详情 | 详情 | |
| (XI) | 59524 | Aminomethylcyclopropane; Cyclopropanemethylamine | 2516-47-4 | C4H9N | 详情 | 详情 |
| (XII) | 64716 | ethyl 2-[3-[bis(tert-butoxycarbonyl)amino]-4-{[(cyclopropylmethyl)amino]sulfonyl}-6-methyl-2-oxo-1(2H)-pyridinyl]acetate | C24H37N3O9S | 详情 | 详情 | |
| (XIII) | 64717 | ethyl 2-[3-amino-4-{[(cyclopropylmethyl)amino]sulfonyl}-6-methyl-2-oxo-1(2H)-pyridinyl]acetate | C14H21N3O5S | 详情 | 详情 | |
| (XIV) | 64718 | 2-[3-amino-4-{[(cyclopropylmethyl)amino]sulfonyl}-6-methyl-2-oxo-1(2H)-pyridinyl]acetic acid | C12H17N3O5S | 详情 | 详情 | |
| (XV) | 18339 | 5-(aminomethyl)-6-methyl-2-pyridinamine; 5-(aminomethyl)-6-methyl-2-pyridinylamine | C7H11N3 | 详情 | 详情 | |
| (XVI) | 64719 | 2-[3-amino-4-{[(cyclopropylmethyl)amino]sulfonyl}-6-methyl-2-oxo-1(2H)-pyridinyl]-N-[(6-amino-2-methyl-3-pyridinyl)methyl]acetamide | C19H26N6O4S | 详情 | 详情 |