Oxalyl chloride → N-(3-Ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79272

反応式

HRID 79272 の反応式
[N:1]1[CH:2]=[C:3]([C:10]([OH:12])=O)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(Cl)(=O)C(Cl)=O.C(N(C(C)C)CC)(C)C.[CH2:28]([C:30]1[C:38]2[C:37]([NH2:39])=[CH:36][CH:35]=[CH:34][C:33]=2[N:32]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([CH3:47])[N:42]=2)[N:31]=1)[CH3:29]>ClCCl.CN(C)C=O>[CH2:28]([C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][C:37]=2[NH:39][C:10]([C:3]2[N:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]3=[N:1][CH:2]=2)=[O:12])[N:32]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([CH3:47])[N:42]=2)[N:31]=1)[CH3:29]

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 73142Imidazo(1,2-a)pyridine-3-carboxylic acidHCID 81531DiisopropylethylamineHCID 672598043-ethyl-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine

生成物 1

HCID 67259302N-(3-Ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide収率 26.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred suspension of imidazo[1,2-a]pyridine-3-carboxylic acid (36.5 mg, 0.225 mmol) in dichloromethane (0.6 mL) was added N,N-dimethylformamide. Oxalyl chloride (84.5 μL, 0.169 mmol) was added and the mixture was stirred in a sealed vessel with ice cooling. The cooling was removed and the mixture was stirred for 3 hours with occasional venting to allow gases to escape. Diisopropylethylamine (21.6 μL, 0.124 mmol) and 3-ethyl-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (30 mg, 0.113 mmol) were added. The mixture was stirred for 30 minutes and then concentrated under reduced pressure. The material was purified using preparative thin layer chromatography, eluting with 10% methanol in dichloromethane containing 0.5% ammonium hydroxide solution. A second purification eluting with 5% methanol in ethyl acetate containing 0.5% ammonium hydroxide solution was carried out to provide N-(3-Ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (12.5 mg). MS (APCI), positive scan, m/z=411.3 (M+H).

後処理

  1. customThe cooling was removed
  2. stirringthe mixture was stirred for 3 hours with occasional venting
  3. stirringThe mixture was stirred for 30 minutes
  4. concentrationconcentrated under reduced pressure
  5. customThe material was purified
  6. washeluting with 10% methanol in dichloromethane containing 0.5% ammonium hydroxide solution
  7. customA second purification
  8. washeluting with 5% methanol in ethyl acetate containing 0.5% ammonium hydroxide solution

出典と根拠

ORDレコード
ord-cae892800fc04d10b4ddef6f348c7bc5
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

関連ノート

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