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【结 构 式】 
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【分子编号】57165 【品名】tert-butyl 2-[(5-cyano-2-pyridinyl)amino]ethylcarbamate 【CA登记号】 |
【 分 子 式 】C13H18N4O2 【 分 子 量 】262.31168 【元素组成】C 59.53% H 6.92% N 21.36% O 12.2% |
合成路线1
该中间体在本合成路线中的序号：(III)The reaction of 6-chloropyridine-3-carbonitrile (I) with carbamate (II) by means of KHCO3 in hot DMF gives the adduct (III), which is treated with TFA in dichloromethane to yield 6-(2-aminoethylamino)pyridine-3-carbonitrile (IV). The cyclization of (IV) with formaldehyde affords 6-(1-imidazoldinyl)pyridine-3-carbonitrile (V), which is condensed with 1-(2-bromoacetyl)piperidine-2(S)-carbonitrile (VI) by means of TEA in THF to provide the adduct (VII). Finally, the cleavage of the imidazolidine ring of (VII) by means of TFA in water, or TFA and 3-(4-(hydrazinosulfonyl)phenyl)propionyl AM resin in dichloromethane, gives rise to the target pyridine-carbonitrile derivative.
| 【1】 Willand, N.; et al.; Solid and solution phase syntheses of the 2-cyanopyrrolidide DPP-IV inhihitor NVP-DPP728. Tetrahedron 2002, 58, 28, 5741. |
| 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) | 57164 | 2-Chloro-5-cyanopyridine; 6-Chloro-3-cyanopyridine; 6-Chloronicotinonitrile | 33252-28-7 | C6H3ClN2 | 详情 | 详情 |
| (II) | 13241 | N-Boc-ethylenediamine;tert-butyl (2-aminoethyl)carbamate；tert-butyl 2-aminoethylcarbamate; tert-Butyl n-(2-aminoethyl)carbamate | 57260-73-8 | C7H16N2O2 | 详情 | 详情 |
| (III) | 57165 | tert-butyl 2-[(5-cyano-2-pyridinyl)amino]ethylcarbamate | C13H18N4O2 | 详情 | 详情 | |
| (IV) | 54332 | 6-[(2-aminoethyl)amino]nicotinonitrile | n/a | C8H10N4 | 详情 | 详情 |
| (V) | 57166 | 6-(1-imidazolidinyl)nicotinonitrile | C9H10N4 | 详情 | 详情 | |
| (VI) | 54334 | (2S)-1-(2-bromoacetyl)-2-pyrrolidinecarbonitrile | n/a | C7H9BrN2O | 详情 | 详情 |
| (VII) | 57167 | 6-(3-{2-[(2S)-2-cyanopyrrolidinyl]-2-oxoethyl}-1-imidazolidinyl)nicotinonitrile | C16H18N6O | 详情 | 详情 |