Triethylamine → 2-[3-(5-Bromo-3-methylpyrid-2-yl)propylamino]-3-nitro-5-(pyrid-3-ylmethyl)pyridine

HRID 1607047

반응식

HRID 1607047 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([Br:12])=[CH:7][N:6]=1.Cl.Cl[C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:18]([CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[CH:17][N:16]=1.C(N(CC)CC)C>C(O)C.NCCCC1C(C)=CC(Br)=CN=1>[Br:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([CH2:4][CH2:3][CH2:2][NH:1][C:15]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:18]([CH2:24][C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=[CH:17][N:16]=2)=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 198517812-(3-Aminopropyl)-5-bromo-3-methylpyridineHCID 198517872-Chloro-3-nitro-5-(pyrid-3-ylmethyl)pyridine hydrochloride

생성물 1

HCID 198517912-[3-(5-Bromo-3-methylpyrid-2-yl)propylamino]-3-nitro-5-(pyrid-3-ylmethyl)pyridine수율 197.5%

시약·촉매·용매 2

HCID 198517812-(3-Aminopropyl)-5-bromo-3-methylpyridine촉매HCID 702Ethanol용매

실험 절차

2-(3-Aminopropyl)-5-bromo-3-methylpyridine (5 g), 2-chloro-3-nitro-5-(pyrid-3-ylmethyl)pyridine hydrochloride (4.45 g) and triethylamine (10 ml) were refluxed together in ethanol (200 ml) for 5.5 hr. A further addition of 2-(3-aminopropyl)-5-bromo-3-methylpyridine (0.5 g) was made and refluxing was continued for a further 2.5 hr. The reaction mixture was then concentrated to dryness giving a yellow oil (13.59 g). The oil was chromatographed on silica in first methanol/chloroform 1:19 increasing the polarity to 1:9. The product was recrystallised from chloroform/petroleum ether (40°-60° C.) to give the title compound (5.11 g), m.p. 105°-106° C.

후처리

  1. temperaturerefluxing
  2. concentrationThe reaction mixture was then concentrated to dryness

출처 및 근거

ORD 기록
ord-caf7841f161a412c91b18e0d52fd35c8
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04863933

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