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Sodium Carbonate → 2-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethylamide

HRID 2112935
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HRID 2112935 반응식
[CH2:1]([NH:3][C:4]([C:6]1[N:11]2[N:12]=[C:13]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])[N:14]=[C:10]2[CH:9]=[C:8](Br)[CH:7]=1)=[O:5])[CH3:2].[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC.O.C(O)C>[Pd](Cl)Cl.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(O)(=O)C>[CH2:1]([NH:3][C:4]([C:6]1[N:11]2[N:12]=[C:13]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])[N:14]=[C:10]2[CH:9]=[C:8]([C:24]2[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=2)[CH:7]=1)=[O:5])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 576430927-Bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethylamideHCID 86587095Dimethoxyethane ethanol water

생성물 1

HCID 251951312-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethylamide

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매
HCID 176Acetic Acid용매

실험 절차

7-Bromo-2-(3-ethyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethylamide (0.160 g, 0.450 mmol), pyridine-3-boronic acid (0.0910 g, 0.742 mmol), sodium carbonate (0.215 g, 2.03 mmol), and bis(diphenylphosphino)ferrocene palladium (II) chloride (0.005 g) were suspended in a solution of ethylene glycol dimethyl ether/water/ethanol (7:3:2, 6.00 mL) and subjected to microwave at 80° C. for 30 minutes. The reaction mixture was acidified with acetic acid and purified by column chromatography (gradient 0-5% methanol/dichloromethane) to afford the desired product 2-(3-ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethylamide MS (APCI+): m/z 354.3 (M+H).

후처리

  1. custompurified by column chromatography (gradient 0-5% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-0672266da5224b098e67095865d4d97c
출처 데이터셋
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07524860B2

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