Coumarin-3-Carboxylic Acid → N-(3-imidazo[1,2-a]pyridin-2-ylphenyl)-2-oxochromene-3-carboxamide

HRID 240040ノート

反応式

HRID 240040 の反応式
CCN(C(C)C)C(C)C.[C:10]([C:13]1[C:14](=[O:23])[O:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:12])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:48]1[C:49]([C:57]2[CH:58]=[C:59]([NH2:63])[CH:60]=[CH:61][CH:62]=2)=[CH:50][N:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=12>CN(C=O)C>[N:48]1[C:49]([C:57]2[CH:58]=[C:59]([NH:63][C:10]([C:13]3[C:14](=[O:23])[O:15][C:16]4[C:21]([CH:22]=3)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[O:12])[CH:60]=[CH:61][CH:62]=2)=[CH:50][N:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=12

参加物

6

反応物 4

HCID 10752Coumarin-3-Carboxylic AcidHCID 81531DiisopropylethylamineHCID 6970213-(Imidazo(1,2-a)pyridin-2-yl)anilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 2877674N-(3-imidazo[1,2-a]pyridin-2-ylphenyl)-2-oxochromene-3-carboxamide収率 85%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

DIEA (50.4 μL, 0.29 mmol) was added to 3-carboxy-coumarin (50.0 mg, 0.26 mmol) and HATU (110.0 mg, 0.29 mmol) in 1 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-Imidazo[1,2-a]pyridin-2-yl-phenylamine (55.0 mg, 0.26 mmol) was added and allowed to react overnight when a solid precipitated out of solution. The resulting precipitate was filtered, dried under suction, and finally dried overnight in vacuo to give 83.6 mg of product in 85% yield: LCMS (ESI) m/z 382 (MH+).

後処理

  1. customresulted
  2. customto react overnight when a solid
  3. customprecipitated out of solution
  4. filtrationThe resulting precipitate was filtered
  5. customdried under suction, and finally dried overnight in vacuo

出典と根拠

ORDレコード
ord-566aa51b423843409ef0908958721c0a
出典データセット
uspto-grants-2014_02
特許番号
US08642788B2

反応ノート

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