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Dimethylacetamide → Ethyl 6-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)-4-phenylpyridine-3-carboxylate

HRID 31939
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인쇄 미리보기

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HRID 31939 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1.[NH2:19][CH2:20][CH2:21][NH:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][N:24]=1.CCN(C(C)C)C(C)C.CC(N(C)C)=O>CCOC(C)=O>[N+:29]([C:26]1[CH:27]=[CH:28][C:23]([NH:22][CH2:21][CH2:20][NH:19][C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:3]=2)=[N:24][CH:25]=1)([O-:31])=[O:30]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 1224252-(2-Aminoethylamino)-5-nitropyridineHCID 22142763Ethyl 6-chloro-4-phenylpyridine-3-carboxylate

생성물 1

HCID 22143004Ethyl 6-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)-4-phenylpyridine-3-carboxylate수율 70%

시약·촉매·용매 1

HCID 8857
Ethyl Acetate
용매

실험 절차

The crude material above, ethyl 6-chloro-4-phenylpyridine-3-carboxylate (140 mg, 0.56 mmol) was mixed with (2-aminoethyl)(5-nitro(2-pyridyl))amine (408 mg, 2.24 mmol), Hünig's base (390 ul), and DMA (2 ml) for 48 hours at 70-75° C. with stirring under argon. The reaction was followed by TLC and HPLC. When judged complete, the reaction was diluted with EtOAc (100 ml) and washed with sat. aq. NaHCO3 (5×30 ml), brine (30 ml), dried with Na2SO4, filtered, and concentrated under reduced pressure. The yellow solid was purified by column chromatography using 5% MeOH in CH2Cl2 as the eluent. The product was dried overnight in vacuo giving ethyl 6-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)-4-phenylpyridine-3-carboxylate in 70% yield.

후처리

  1. washwashed with sat. aq. NaHCO3 (5×30 ml), brine (30 ml)
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe yellow solid was purified by column chromatography
  6. customThe product was dried overnight in vacuo

출처 및 근거

ORD 기록
ord-7ad28e6003144e34a8b89ccba300464e
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07425557B2

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