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【结 构 式】

【分子编号】58807

【品名】tert-butyl 3-methoxy-5-nitrobenzyl[4-(4-morpholinyl)-6-({[2-(trimethylsilyl)ethoxy]methoxy}methyl)-2-pyridinyl]carbamate

【CA登记号】

【 分 子 式 】C29H44N4O8Si

【 分 子 量 】604.77602

【元素组成】C 57.59% H 7.33% N 9.26% O 21.16% Si 4.64%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XI)

The condensation of 4-chloro-2,6-pyridinedicarboxylic acid (I) with morpholine (II) afforded the morpholinopyridinedicarboxylic acid (III), which was further esterified with MeOH and HCl to produce diester (IV). Reduction of (IV) with NaBH4 and CaCl2 gave hydroxy ester (V). After protection of the hydroxyl group of (V) as the trimethylsilylethoxymethyl derivative (VII), the ester group was hydrolyzed under basic conditions yielding acid (VIII). This was then subjected to a Curtius rearrangement with DPPA in the presence of tert-butanol to generate the tert-butyl carbamate (IX). Alkylation of carbamate (IX) with 3-methoxy-5-nitrobenzyl bromide (X) and NaH furnished the N-benzyl carbamate derivative (XI). The nitro group of (XI) was then reduced to amine (XII) by catalytic hydrogenation over Pd/C.

1 Fukami, T.; Mase, T.; Tsuchiya, Y.; Kanatani, A.; Fukuroda, T. (Banyu Pharmaceutical Co., Ltd.); Aminopyridine derivs.. EP 0889034; US 6011039; WO 9734873 .
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) 58799 4-chloro-2,6-pyridinedicarboxylic acid C7H4ClNO4 详情 详情
(II) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(III) 58800 4-(4-morpholinyl)-2,6-pyridinedicarboxylic acid C11H12N2O5 详情 详情
(IV) 58801 dimethyl 4-(4-morpholinyl)-2,6-pyridinedicarboxylate C13H16N2O5 详情 详情
(V) 58802 ethyl 6-(hydroxymethyl)-4-(4-morpholinyl)-2-pyridinecarboxylate C13H18N2O4 详情 详情
(VI) 27243 [2-(chloromethoxy)ethyl](trimethyl)silane 76513-69-4 C6H15ClOSi 详情 详情
(VII) 58803 ethyl 4-(4-morpholinyl)-6-({[2-(trimethylsilyl)ethoxy]methoxy}methyl)-2-pyridinecarboxylate C19H32N2O5Si 详情 详情
(VIII) 58804 4-(4-morpholinyl)-6-({[2-(trimethylsilyl)ethoxy]methoxy}methyl)-2-pyridinecarboxylic acid C17H28N2O5Si 详情 详情
(IX) 58805 tert-butyl 4-(4-morpholinyl)-6-({[2-(trimethylsilyl)ethoxy]methoxy}methyl)-2-pyridinylcarbamate C21H37N3O5Si 详情 详情
(X) 58806 3-(bromomethyl)-5-nitrophenyl methyl ether; 1-(bromomethyl)-3-methoxy-5-nitrobenzene C8H8BrNO3 详情 详情
(XI) 58807 tert-butyl 3-methoxy-5-nitrobenzyl[4-(4-morpholinyl)-6-({[2-(trimethylsilyl)ethoxy]methoxy}methyl)-2-pyridinyl]carbamate C29H44N4O8Si 详情 详情
(XII) 58808 tert-butyl 3-amino-5-methoxybenzyl[4-(4-morpholinyl)-6-({[2-(trimethylsilyl)ethoxy]methoxy}methyl)-2-pyridinyl]carbamate C29H46N4O6Si 详情 详情
Extended Information