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Triethylamine → N-methoxy-N-methyl-2-oxo-1,2-dihydropyridine-4-carboxamide

HRID 626201
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HRID 626201 반응식
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][NH:3]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:33][O:34][NH:35][CH3:36].CCN(CC)CC>C(Cl)Cl>[CH3:33][O:34][N:35]([CH3:36])[C:8]([C:6]1[CH:5]=[CH:4][NH:3][C:2](=[O:1])[CH:7]=1)=[O:10]
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참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2807562-Hydroxyisonicotinic Acid

생성물 1

HCID 89655466N-methoxy-N-methyl-2-oxo-1,2-dihydropyridine-4-carboxamide수율 60%
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시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 2-oxo-1,2-dihydropyridine-4-carboxylic acid (8.0 g, 1.0 eq), EDCI (13.2 g, 1.2 eq) and HOBt (9.3 g, 1.2 eq) in 150 mL CH2Cl2 were added N-methoxymethanamine hydrochloride (6.8 g, 1.2 eq) and Et3N (26.2 g, 4.5 eq). The reaction mixture was stirred at rt overnight, concentrated, and purified by column chromatography to give the desired product (6.3, 60% yield). 1H NMR (400 MHz, CDCl3) δ 12.79 (s, 1H), 7.40 (d, J=6.8 Hz, 1H), 6.77 (s, 1H), 6.43 (dd, J=6.8 Hz, 1.6 Hz, 1H), 3.62 (s, 3H), 3.34 (s, 3H).

후처리

  1. concentrationconcentrated
  2. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-cbd070787a61443098960d8247421e50
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309211B2

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