Diisopropylethylamine → N-(3-(imidazo[1,2-a]pyridin-2-yl)phenyl)-8-methoxy-2-oxo-2H-chromene-3-carboxamide

HRID 240008

反応式

HRID 240008 の反応式
C(N(C(C)C)CC)(C)C.[CH3:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[O:20][C:19](=[O:22])[C:18]([C:23]([OH:25])=O)=[CH:17]2.[N:26]1[C:27]([C:35]2[CH:36]=[C:37]([NH2:41])[CH:38]=[CH:39][CH:40]=2)=[CH:28][N:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=12>CN(C)C=O>[N:26]1[C:27]([C:35]2[CH:36]=[C:37]([NH:41][C:23]([C:18]3[C:19](=[O:22])[O:20][C:21]4[C:16]([CH:17]=3)=[CH:15][CH:14]=[CH:13][C:12]=4[O:11][CH3:10])=[O:25])[CH:38]=[CH:39][CH:40]=2)=[CH:28][N:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=12

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 2345628-Methoxy-2-oxo-2H-chromene-3-carboxylic acidHCID 6970213-(Imidazo(1,2-a)pyridin-2-yl)aniline

生成物 1

HCID 43816622N-(3-(imidazo[1,2-a]pyridin-2-yl)phenyl)-8-methoxy-2-oxo-2H-chromene-3-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Diisopropylethylamine (DIEA, 0.044 mL, 0.25 mmol) was added to 8-methoxy-3-carboxy-coumarin (0.05 g, 0.23 mmol) and O-(7-Azabenzotriazole-1-yl)-N,N,N,N′-tetramethyluronium hexafluorophosphate (HATU, 0.096 g, 0.25 mmol) in 2 mL of dimethylformamide (DMF) with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-Imidazo[1,2-a]pyridin-2-yl-phenylamine (0.048 g, 0.023 mmol) was added and allowed to react for approximately 30 minutes, when a yellow solid precipitated out of solution. The precipitate was filtered and dried under suction and then in vacuo to give 1541: 1H NMR (400 MHz, DMSO-d6) δ 10.78 (s, 1H), 8.92 (s, 1H), 8.54 (d, J=7.0 Hz, 1H), 8.44 (s, 1H), 8.31 (s, 1H), 7.73 (m, 2H), 7.60 (d, J=9.0 Hz, 1H), 7.57 (d, J=9.0 Hz, 1H), 7.44 (m, 3H), 7.26 (dd, J=5.5, 6.8 Hz, 1H), 6.90 (dd, J=5.5, 6.8 Hz, 1H), 3.96 (s, 3H); LCMS (ESI) m/z 412 (MH+).

後処理

  1. customresulted
  2. customto react for approximately 30 minutes
  3. customwhen a yellow solid precipitated out of solution
  4. filtrationThe precipitate was filtered
  5. customdried under suction
  6. customin vacuo to give 1541

出典と根拠

ORDレコード
ord-ec82a635a1a94ca1a34a929cb9925964
出典データセット
uspto-grants-2014_02
特許番号
US08642788B2

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