O-(环戊基甲基)羟胺盐酸盐 → n-Cyclopentylmethoxy-2-[(2-methanesulfonylamino-pyridin-4-ylmethyl)-amino]-benzamide

HRID 1663166笔记

反应方程式

HRID 1663166 反应方程式
O=C1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:10]=2)[C:6]2[CH:20]=[CH:21][CH:22]=[CH:23][C:5]=2[C:4](=[O:24])O1.Cl.[CH:26]1([CH2:31][O:32][NH2:33])[CH2:30][CH2:29][CH2:28][CH2:27]1>>[CH:26]1([CH2:31][O:32][NH:33][C:4](=[O:24])[C:5]2[CH:23]=[CH:22][CH:21]=[CH:20][C:6]=2[NH:7][CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])[CH:10]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1

参与物

3

反应物 2

HCID 53399251O-(环戊基甲基)羟胺盐酸盐HCID 86615647N-[4-(2,4-dioxo-4H-benzo[d][1,3]oxazin-1-ylmethyl)-pyridin-2-yl]-methanesulfonamide

产物 1

HCID 44553342n-Cyclopentylmethoxy-2-[(2-methanesulfonylamino-pyridin-4-ylmethyl)-amino]-benzamide

实验过程

To a stirred solution of 1-(2-amino-pyridin-4-ylmethyl)-1H-benzo[d][1,3]oxazine-2,4-dione (600 mg, see preparation 7b) in pyridine (7 ml) was added methanesulfonyl chloride (280 mg) and the reaction mixture was stirred at room temperature for 15 hours. The solvent was evaporated under reduced pressure and the residue was dissolved in EtOAc and washed with water and brine. The organic layer was dried (MgSO4) and evaporated under reduced pressure. The remaining solid yellow material was dissolved in a mixture of hot EtOAc (50 ml) and DMF (4 ml). On cooling a solid material formed, that was isolated by filtration and dried under vacuum, affording N-[4-(2,4-dioxo-4H-benzo[d][1,3]oxazin-1-ylmethyl)-pyridin-2-yl]-methanesulfonamide. Step 2: This anhydride intermediate was converted into the title compound by reaction with O-cyclopentylmethyl-hydroxylamine hydrochloride (see preparation 66), using general procedure 1A. 13C-NMR (DMSO-d6) δ 166.8, 152.9, 152.6, 148.3, 132.4, 127.9, 115.2, 114.8, 113.3, 111.4, 110.1, 79.4, 45.0, 41.5, 37.6, 28.9, 24.9.

来源与证据

ORD记录
ord-a6d92be292874ac4b9af546d73ffe9df
来源数据集
uspto-grants-2011_10
专利号
US08034811B2

反应笔记

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