|
【结 构 式】 
|
【分子编号】19538 【品名】5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole 【CA登记号】7305-71-7 |
【 分 子 式 】C4H6N2S 【 分 子 量 】114.17112 【元素组成】C 42.08% H 5.3% N 24.54% S 28.09% |
与该中间体有关的原料药合成路线共 7 条
合成路线1
该中间体在本合成路线中的序号：(III)The synthesis of meloxicam is performed as follows: The reaction of benzisothiazolo-3(2H)-one-1,1-dioxide (I) with methyl chloroacetate gives the methyl 2(3H)-acetate derivative, which is isomerized with sodium methoxide in toluene/tert-butanol yielding methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide. The subsequent methylation with methyl iodide in methanol yields 2-methyl compound (II). Finally, this compound is treated with 2-amino-5-methylthiazole in xylene.
| 【1】 Trummlitz, G.; Engelhardt, G.; Busch, U.; MELOXICAM < Rec INN >. Drugs Fut 1989, 14, 11, 1047. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 11298 | 1H-1,2-Benzisothiazole-1,1,3(2H)-trione; Saccharin | 81-07-2 | C7H5NO3S | 详情 | 详情 |
| (II) | 19537 | methyl 4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylate | C11H11NO5S | 详情 | 详情 | |
| (III) | 19538 | 5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole | 7305-71-7 | C4H6N2S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)
| 【1】 Zia-ur-Rehman M, Choudary JA, Ahmad S 2005. Applied chemistry research center, lahore, pak. An efficient synthysis of 2-alkyl-4-hydroxy2H-l, 2-benzothiazine-3-carboxamide-l, l-dioxides. Bull Korean Chem Soc, 26: 1771～1775 |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 40062 | methyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)acetate | 6639-62-9 | C10H9NO5S | 详情 | 详情 |
| (II) | 66516 | methyl 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide | 35511-14-9 | C10H9NO5S | 详情 | 详情 |
| (III) | 19537 | methyl 4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylate | C11H11NO5S | 详情 | 详情 | |
| (IV) | 19538 | 5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole | 7305-71-7 | C4H6N2S | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(V)
| 【1】 Wu，Fan-hong Wang，Bao-dan. Xi，Guan-gen．2002．Synthesis of meloxicam and piroxicam．华东理工大学学报，28: 282～284 |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 11298 | 1H-1,2-Benzisothiazole-1,1,3(2H)-trione; Saccharin | 81-07-2 | C7H5NO3S | 详情 | 详情 |
| (II) | 66518 | isopropyl 2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)acetate | C12H13NO5S | 详情 | 详情 | |
| (III) | 66519 | isopropyl 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide | 76508-35-5 | C12H13NO5S | 详情 | 详情 |
| (IV) | 66519 | isopropyl 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide | 76508-35-5 | C12H13NO5S | 详情 | 详情 |
| (V) | 19538 | 5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole | 7305-71-7 | C4H6N2S | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(IV)
| 【1】 Wang YC, Shi DQ, Zhao H et aL.2001. Synthesis of meloxicam. 中国医药工业杂志．32: 244～245 |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 29338 | 1-propanol | 71-23-8 | C3H8O | 详情 | 详情 |
| (II) | 15966 | propionaldehyde | 123-38-6 | C3H6O | 详情 | 详情 |
| (III) | 66520 | 3,3-dibromopropanal | C3H4Br2O | 详情 | 详情 | |
| (IV) | 19538 | 5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole | 7305-71-7 | C4H6N2S | 详情 | 详情 |
| (V) | 19537 | methyl 4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylate | C11H11NO5S | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(V)
| 【1】 Zhang L. Xie LH，Hua ZM et aL 2000．Synthesis of meloxicanm. 中国医药工业杂志，31: 481～483 |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 66519 | isopropyl 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide | 76508-35-5 | C12H13NO5S | 详情 | 详情 |
| (I) | 11298 | 1H-1,2-Benzisothiazole-1,1,3(2H)-trione; Saccharin | 81-07-2 | C7H5NO3S | 详情 | 详情 |
| (II) | 40062 | methyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)acetate | 6639-62-9 | C10H9NO5S | 详情 | 详情 |
| (III) | 66516 | methyl 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide | 35511-14-9 | C10H9NO5S | 详情 | 详情 |
| (V) | 19538 | 5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole | 7305-71-7 | C4H6N2S | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(II)
| 【1】 Trummlitz G, Engel W, Seeger E et aL 1980. 4-Hydroxy-2H-1,2-benzothiazine-3-carboxamide-l,l-dioxides and salts thereof. US 4233299 |
合成路线7
该中间体在本合成路线中的序号：(VI)
| 【1】 Hill JH M. 1965. Mechanism of the gabriel-colman rearrangement. J Org Chem, 30: 620～622 |
| 【2】 Wen YZ, Wei WL, Gao ZW. 2005. Synthesis of meloxicam．中国医药工业杂志．36 (6): 321～322 |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 66516 | methyl 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide | 35511-14-9 | C10H9NO5S | 详情 | 详情 |
| (I) | 66521 | C7H4KN2O3 | 详情 | 详情 | ||
| (II) | 10257 | methyl 2-chloroacetate; methyl chloroacetate | 96-34-4 | C3H5ClO2 | 详情 | 详情 |
| (III) | 66522 | C10H9N2O5 | 详情 | 详情 | ||
| (V) | 19537 | methyl 4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1lambda(6),2-benzothiazine-3-carboxylate | C11H11NO5S | 详情 | 详情 | |
| (VI) | 19538 | 5-Methyl-2-thiazolamine; 5-methyl-1,3-thiazol-2-ylamine; 5-methyl-1,3-thiazol-2-amine; 2-amino-5-methylthiazole | 7305-71-7 | C4H6N2S | 详情 | 详情 |
Extended Information