D-19050, -Drug Synthesis Database

【结构式】

【药物名称】D-19050

【化学名称】2-Amino-3-[(prop-1-en-3-yl)oxycarbonylamino]-6-(4-fluorobenzylamino)pyridine hydrochloride
　　　　　　Prop-1-en-3-yl [N-[2-amino-6-(4-fluorobenzylamino)pyridin-3-yl]]carbamate hydrochloride
　　　　　　2-Amino-6-[(4-fluorophenylmethyl)amino]-3-pyridylcarbamic acid (prop-1-en-3-yl)ester hydrochloride
　　　　　　2-Amino-6-(4-Fluorobenzylamino)-3-(2-propenyloxycarbonylamino)pyridine hydrochloride
　　　　　　N-[2-Amino-6-(4-fluorobenzylamino)pyridin-3-yl]carbamic acid 2-propenyl ester hydrochloride

【CA登记号】149690-78-8

【分子式】C₁₆H₁₈ClFN₄O₂

【分子量】352.79886

【开发单位】Asta Medica (Originator)

【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Non-Opioid Analgesics

合成路线1

D-19050 can be obtained in a 5-step synthesis starting from 2,6-dichloropyridine (I): Compound (I) is nitrated with HNO3/H2SO4 yielding 2,6-dichloro-3-nitropyridine (II). Subsequent reaction with ammonia and 4-fluorobenzylamine leads to 2-amino-3-nitro-6-(4-fluorobenzylamino)pyridine (IV), which is hydrogenated using Raney Nickel as catalyst to the corresponding 3-amino derivative (V). This is not isolated, but reacted with (prop-1-en-3-yl)chloroformate to give D-19050.

参考文献中间体

【1】 Engel, J.; Emig, P.; Szelenyi, I.; Nickel, B.; Weischer, K.H.; D-19050. Drugs Fut 1989, 14, 6, 511.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	31095	4-fluorobenzylamine; (4-fluorophenyl)methanamine	140-75-0	C₇H₈FN	详情	详情
(I)	13573	2,6-Dichloropyridine	2402-78-0	C₅H₃Cl₂N	详情	详情
(II)	13574	2,6-Dichloro-3-nitropyridine	16013-85-7	C₅H₂Cl₂N₂O₂	详情	详情
(III)	13575	6-Chloro-3-nitro-2-pyridinamine; 2-Amino-6-chloro-3-nitropyridine; 6-Chloro-3-nitro-2-pyridinylamine	27048-04-0	C₅H₄ClN₃O₂	详情	详情
(IV)	13576	N(6)-(4-Fluorobenzyl)-3-nitro-2,6-pyridinediamine; N-(6-Amino-5-nitro-2-pyridinyl)-N-(4-fluorobenzyl)amine		C₁₂H₁₁FN₄O₂	详情	详情
(V)	13577	N(6)-(4-Fluorobenzyl)-2,3,6-pyridinetriamine; 2-Amino-6-[(4-fluorobenzyl)amino]-3-pyridinylamine		C₁₂H₁₃FN₄	详情	详情

Extended Information