1,2-Dichloroethane → Methyl 3-[(methylamino)carbonyl]-5-(5-methylpyridin-2-yl)benzoate

HRID 888381ノート

反応式

HRID 888381 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=2)[CH:13]=1)[C:8](O)=[O:9])=[O:4].N.O1CCOCC1.C(Cl)CCl.C1C=CC2N(O)N=[N:38][C:36]=2C=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:36][NH:38][C:8]([C:7]1[CH:6]=[C:5]([CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=2)[CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])=[O:9]

参加物

8

反応物 6

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 312751,4-DioxaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 684994173-(Methoxycarbonyl)-5-(5-methylpyridin-2-yl)benzoic acid

生成物 1

HCID 68496788Methyl 3-[(methylamino)carbonyl]-5-(5-methylpyridin-2-yl)benzoate収率 93.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-(methoxycarbonyl)-5-(5-methylpyridin-2-yl)benzoic acid (1.85 g, 6.82 mmol) in N,N-dimethylformamide (20 mL) was added 2 M ammonia in dioxane (10.2 mL, 20.4 mmol), EDC (2.61 g, 13.6 mmol), HOBT (2.09 g, 13.6 mmol) and N,N-diisopropylethylamine (4.76 mL, 27.3 mmol). After 16 h, the reaction was concentrated and the residue was dissolved in 200 ml of dichloromethane. The mixture was washed with 100 mL of saturated aqueous sodium bicarbonate solution (2×) and brine (100 ml). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (1% ethyl acetate/hexane→60% ethyl acetate/hexane) to give the title compound (1.82 g). MS 285.1 (M+1).

後処理

  1. concentrationthe reaction was concentrated
  2. dissolutionthe residue was dissolved in 200 ml of dichloromethane
  3. washThe mixture was washed with 100 mL of saturated aqueous sodium bicarbonate solution (2×) and brine (100 ml)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (1% ethyl acetate/hexane→60% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-56d7b4349c594464979d9dc1d0a41253
出典データセット
uspto-grants-2012_08
特許番号
US08247401B2

反応ノート

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