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Water → N-{6-[(Phenylmethyl)oxy]-3-pyridinyl}acetamide

HRID 1173445
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HRID 1173445 반응식
[C:1]1([CH2:7][O:8][C:9]2[N:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH3:22][C:23](OC(C)=O)=[O:24].O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]1([CH2:7][O:8][C:9]2[N:14]=[CH:13][C:12]([NH:15][C:23](=[O:24])[CH3:22])=[CH:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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참가 물질

7

반응물 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 5632866-(Benzyloxy)pyridin-3-amine

생성물 1

HCID 59557134N-{6-[(Phenylmethyl)oxy]-3-pyridinyl}acetamide수율 94.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6344
Dichloromethane
용매

실험 절차

To a solution of 6-[(phenylmethyl)oxy]-3-pyridinamine (0.213 g, 1.07 mmol; step B above) in CH2Cl2 (5 mL) at rt was added pyridine (0.17 mL, 2.14 mmol), DMAP (0.0065 g, 0.050 mmol) and Ac2O (0.12 mL, 1.28 mmol). After 5 min the mixture was poured into water and extracted with CH2Cl2 (×3). The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.245 g of the title compound as a colorless solid: MS (ESI) m/z 243 (M+1).

후처리

  1. extractionextracted with CH2Cl2 (×3)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-fbe762f59ce64575bdcf6a0ff871a5e8
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07834063B2

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