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N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide → N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)acetamide

HRID 2278928
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HRID 2278928 반응식
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:10]=2)=[CH:6][CH:5]=[C:4]([N+:19]([O-])=O)[N:3]=1>CO.[Pd]>[NH2:19][C:4]1[N:3]=[C:2]([CH3:1])[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:10]=2)=[CH:6][CH:5]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 1

HCID 90410470N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide

생성물 1

HCID 90426152N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)acetamide수율 94%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A solution of N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide (0.44 g, 1.526 mmol) in MeOH (30 mL) was treated with palladium on carbon (50% wet, 0.162 g, 0.153 mmol) and hydrogenated (1 atm) at RT for 24 h. The solids were removed via filtration through diatomaceous earth, washed well with MeOH and the filtrate concentrated to afford N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)acetamide (370 mg, 94%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.46 (s, 1 H), 8.10 (d, J=5.7 Hz, 1 H), 7.53 (d, J=2.3 Hz, 1 H), 7.13 (d, J=8.7 Hz, 1 H), 6.53 (dd, J=5.7, 2.4 Hz, 1 H), 6.32 (d, J=8.7 Hz, 1 H), 5.91 (s, 2 H), 2.02 (s, 3 H), 2.01 (s, 3 H); MS (ESI) m/z: 259.2 (M+H+).

후처리

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washwashed well with MeOH
  3. concentrationthe filtrate concentrated

출처 및 근거

ORD 기록
ord-d63040840bed43c692c49d42aea199fa
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133183B2

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