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1,2-Dichloroethane → 2-Morpholin-4-yl-propionic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

HRID 2285000
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HRID 2285000 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[N:10]1([CH:16]([CH3:20])[C:17](O)=[O:18])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.C(Cl)CCl>C(Cl)Cl.[Cl-].[Na+].O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:17](=[O:18])[CH:16]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH3:20])=[N:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 31525652-Morpholin-4-ylpropanoic acidHCID 199167865-Fluoro-2-hydrazinylpyridine

생성물 1

HCID 866870312-Morpholin-4-yl-propionic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide수율 99.9%

시약·촉매·용매 3

HCID 962Water용매2회HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of (5-fluoro-pyridin-2-yl)-hydrazine (1.62 g, 12.8 mmol), 2-(morpholin-4-yl)propanoic acid (Enamine, 2.50 g, 12.8 mmol), HOBt.H2O (196 mg, 1.28 mmol) and Et3N (2.14 mL, 15.3 mmol) in DCM (50 mL) was added EDC (2.94 g, 15.3 mmol) and the brown solution stirred at RT for 16 h. Water (20 mL) and brine (20 mL) were added, and the mixture shaken. The aqueous layer was extracted with DCM (20 mL), then the combined organics were passed through a hydrophobic frit and concentrated in vacuo to give the title compound as a brown foam (3.43 g, >99%). LCMS (Method 3): Rt 0.44 min, m/z 269 [MH+].

후처리

  1. stirringthe mixture shaken
  2. extractionThe aqueous layer was extracted with DCM (20 mL)
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-dd93d1a272514a0486c110be02408608
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09145413B2

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