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Ammonia → 5-[2-(Acetylamino)pyridin-4-yl]-2-(2-chlorophenyl)-3-furamide

HRID 537036
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HRID 537036 반응식
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])=[C:13]([C:23]([OH:25])=O)[CH:12]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].N.C[N:28](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CC(N(C)C)=O>C(Cl)Cl.O>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])=[C:13]([C:23]([NH2:28])=[O:25])[CH:12]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 31374DimethylacetamideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 667483155-[2-(Acetylamino)pyridin-4-yl]-2-(2-chlorophenyl)-3-furoic acid

생성물 1

HCID 568393735-[2-(Acetylamino)pyridin-4-yl]-2-(2-chlorophenyl)-3-furamide수율 62.2%

시약·촉매·용매 2

HCID 962Water용매
HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-[2-(acetylamino)pyridin-4-yl]-2-(2-chlorophenyl)-3-furoic acid (0.10 g, 0.28 mmol) in DCM (15 mL) was added ammonia (0.5 M in 1,4-dioxane, 4.5 mL), TBTU (0.18 g, 0.56 mmol) and DMA (0.49 mL, 2.8 mmol). The mixture was allowed to stir at rt overnight. The reaction mixture was diluted with water and extracted with DCM. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 5-[2-(acetylamino)pyridin-4-yl]-2-(2-chlorophenyl)-3-furamide (0.062 g, 62%) as a white solid. LCMS (FA): m/z=356.5 (M+H).

후처리

  1. extractionextracted with DCM
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-4a6186c298a94036973e99807771297a
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08859768B2

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