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【结 构 式】 
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【分子编号】53958 【品名】5-({[2-(1-methyl-2-pyrrolidinyl)ethyl]amino}sulfonyl)-2-propoxy-1-benzenecarboxylic 2,4,6-trichloro-1-benzenecarboxylic anhydride 【CA登记号】n/a |
【 分 子 式 】C24H27Cl3N2O6S 【 分 子 量 】577.91236 【元素组成】C 49.88% H 4.71% Cl 18.4% N 4.85% O 16.61% S 5.55% |
合成路线1
该中间体在本合成路线中的序号：(V)The reaction of 5-(chlorosulfonyl)-2-propoxybenzoic acid (I) with 2-(1-methylpyrrolidin-2-yl)ethylamine (II) in acetone gives the sulfonamide (III), which is treated with 2,4,6-trichlorobenzozyl chloride (IV) and TEA to afford the active mixed anhydride (V). The condensation of (V) with 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide (VI) in dichloromethane provides the corresponding carboxamide (VII). Finally, this compound is cyclized by means of tBu-OK in refluxing tert-butanol to furnish the target pyrrolo-pyrimidinone.
| 【1】 Kim, S.; Kim, H.; Kim, D.S.; Chang, M.S.; Yoo, M.; Lim, J.I.; Ahn, B.O.; Kim, W.; Kim, I.Y.; Lim, T.K.; Kang, K.K.; Son, M.; Doh, M.; Shim, H.; Oh, T.; Kim, D.G. (Dong-A Pharmaceutical Co., Ltd.); Pyrazolopyrimidinone derivs. for the treatment of impotence. EP 1129093; WO 0027848 . |
| 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) | 53956 | 5-(chlorosulfonyl)-2-propoxybenzoic acid | C10H11ClO5S | 详情 | 详情 | |
| (II) | 53954 | 2-(2-Aminoethyl)-1-methylpyrrolidine | n/a | C7H16N2 | 详情 | 详情 |
| (III) | 53957 | 5-({[2-(1-methyl-2-pyrrolidinyl)ethyl]amino}sulfonyl)-2-propoxybenzoic acid | n/a | C17H26N2O5S | 详情 | 详情 |
| (IV) | 25718 | 2,4,6-trichlorobenzoyl chloride | 4136-95-2 | C7H2Cl4O | 详情 | 详情 |
| (V) | 53958 | 5-({[2-(1-methyl-2-pyrrolidinyl)ethyl]amino}sulfonyl)-2-propoxy-1-benzenecarboxylic 2,4,6-trichloro-1-benzenecarboxylic anhydride | n/a | C24H27Cl3N2O6S | 详情 | 详情 |
| (VI) | 15627 | 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide; 4-amino-1-methyl-3-propyl-5-pyrazolecarboxamide | 139756-02-8 | C8H14N4O | 详情 | 详情 |
| (VII) | 53955 | 1-methyl-4-{[5-({[2-(1-methyl-2-pyrrolidinyl)ethyl]amino}sulfonyl)-2-propoxybenzoyl]amino}-3-propyl-1H-pyrazole-5-carboxamide | C25H38N6O5S | 详情 | 详情 |