4-Methoxybenzylamine → N-(4-methoxybenzyl)-5-bromo-3-(5-(2,3-dichlorophenyl)thiazol-4-yl)pyridin-2-amine

HRID 1518531노트

반응식

HRID 1518531 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[CH:11][S:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[Cl:21])[C:5](Cl)=[N:6][CH:7]=1.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>COCCOC>[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][C:5]2[C:4]([C:9]3[N:10]=[CH:11][S:12][C:13]=3[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=3[Cl:21])=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[CH:26][CH:25]=1

참가 물질

4

반응물 2

HCID 754524-MethoxybenzylamineHCID 581800755-Bromo-2-chloro-3-(5-(2,3-dichlorophenyl)thiazol-4-yl)pyridine

생성물 1

HCID 58179565N-(4-methoxybenzyl)-5-bromo-3-(5-(2,3-dichlorophenyl)thiazol-4-yl)pyridin-2-amine수율 85%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of 5-bromo-2-chloro-3-(5-(2,3-dichlorophenyl)thiazol-4-yl)pyridine (520 mg, 1.24 mmol) and p-methoxybenzyl amine (373 mg, 2.72 mmol) in DME (12 mL) was stirred at 80° C. for 48 hours. The reaction mixture was concentrated and the residue purified by silica gel chromatography (0-25% EtOAc/hexanes) to give N-(4-methoxybenzyl)-5-bromo-3-(5-(2,3-dichlorophenyl)thiazol-4-yl)pyridin-2-amine as a pale yellow solid [631 mg, 85% yield; LC-MS, M+H=519.9; 1H-NMR (300 MHz, CDCl3) 8.85 (1 H, s), 8.00 (1 H, d, J=2.3 Hz), 7.45 (1H, dd, J=1.9, 7.6 Hz), 7.10-7.17 (4 H, m), 7.01 (1 H, d, J=2.4 Hz), 6.77 (1 H, t, J=6.7 Hz)].

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by silica gel chromatography (0-25% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-c5fc8f3308ad4bcf9841ee0350f343a3
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232406B2

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