phenyl 4-cyano-3-methoxyphenylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】61933

【品名】phenyl 4-cyano-3-methoxyphenylcarbamate

【CA登记号】

【分子式】C₁₅H₁₂N₂O₃

【分子量】268.27196

【元素组成】C 67.16% H 4.51% N 10.44% O 17.89%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

The intermediate carbamate (V) has been obtained as follows. The reaction of 4-bromo-3-methoxynitrobenzene (I) with CuCN in NMP at 150 C gives 2-methoxy-4-nitrobenzonitrile (II), which is reduced with H2 over Pd/C in ethyl acetate to yield 4-amino-2-methoxybenzonitrile (III). Finally, this compound is condensed with phenyl carbamate (IV) by means of NaHCO3 in ethyl acetate to afford the desired carbamate intermediate (V).

参考文献中间体

合成目标

【1】 Saunders, J.; Bethiel, S.; Badia, M.; Stamos, D.; Trudeau, M. (Vertex Pharmaceuticals Inc.); Inhibitors of IMPDH enzyme. WO 0056331 .

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)	51316	2-Bromo-5-nitroanisole	77337-82-7	C₇H₆BrNO₃	详情	详情
(II)	61931	2-methoxy-4-nitrobenzonitrile		C₈H₆N₂O₃	详情	详情
(III)	61932	4-amino-2-methoxybenzonitrile		C₈H₈N₂O	详情	详情
(IV)	33820	phenyl carbamate	622-46-8	C₇H₇NO₂	详情	详情
(V)	61933	phenyl 4-cyano-3-methoxyphenylcarbamate		C₁₅H₁₂N₂O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

The reduction of 3-nitroacetophenone (VI) by means of NaBH4 in ethanol gives 1-(3-nitrophenyl)ethanol (VII), which is treated with DPPA and DBU in hot toluene to yield the azido derivative (VIII). The reduction of (VIII) with PPh3 in THF/water affords 1-(3-nitrophenyl)ethylamine (IX) as a racemic mixture that is submitted to optical resolution with L-(+)-tartaric acid to provide the desired (S)-isomer (X). The reduction of the nitro group of (X) by means of H2 over Pd/C in methanol gives 1(S)-(3-aminophenyl)ethylamine (XI), which is condensed with 2(R)-hydroxypentanenitrile (XII) and CDI to yield the carbamate (XIII). Finally, this compound is condensed with intermediate carbamate (V) by means of TEA in hot ethyl acetate to afford the target urea.

参考文献中间体

合成目标

【1】 Saunders, J.; Bethiel, S.; Badia, M.; Stamos, D.; Trudeau, M. (Vertex Pharmaceuticals Inc.); Inhibitors of IMPDH enzyme. WO 0056331 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	61933	phenyl 4-cyano-3-methoxyphenylcarbamate		C₁₅H₁₂N₂O₃	详情	详情
(VI)	61934	1-(3-nitrophenyl)-1-ethanone；3-Nitroacetophenone;m-Nitroacetophenone	121-89-1	C₈H₇NO₃	详情	详情
(VII)	61935	1-(3-nitrophenyl)-1-ethanol		C₈H₉NO₃	详情	详情
(VIII)	61936	1-(1-azidoethyl)-3-nitrobenzene		C₈H₈N₄O₂	详情	详情
(IX)	61937	1-(3-nitrophenyl)ethylamine; 1-(3-nitrophenyl)-1-ethanamine		C₈H₁₀N₂O₂	详情	详情
(X)	61938	(1S)-1-(3-nitrophenyl)-1-ethanamine; (1S)-1-(3-nitrophenyl)ethylamine		C₈H₁₀N₂O₂	详情	详情
(XI)	61939	3-[(1S)-1-aminoethyl]aniline; 3-[(1S)-1-aminoethyl]phenylamine		C₈H₁₂N₂	详情	详情
(XII)	61940	(3R)-3-hydroxypentanenitrile		C₅H₉NO	详情	详情
(XIII)	61941	(1R)-1-(cyanomethyl)propyl (1S)-1-(3-aminophenyl)ethylcarbamate		C₁₄H₁₉N₃O₂	详情	详情

Extended Information