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

HRID 537036
ノート
印刷プレビュー

反応式

HRID 537036 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4a6186c298a94036973e99807771297a
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08859768B2

反応ノート

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