1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 1-(4-fluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 347542

反応式

HRID 347542 の反応式
O=[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][O:3]1.[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.CCN=C=NCCCN(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:18]2[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:2]2=[O:3])=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 673264-FluorobenzylamineHCID 117704Methyl 2-oxo-2H-pyran-3-carboxylate

生成物 1

HCID 21081722Methyl 1-(4-fluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylate収率 73.6%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

A heterogeneous mixture of methyl 2-oxo-2H-pyran-3-carboxylate (2.0 g, 13 mmol, 1.0 eq, Aldrich) and 4-fluorobenzylamine (1.5 mL, 13 mmol, 1.0 eq) in DMF (10 mL) was stirred at room temperature for 3 h. The reaction mixture was treated with EDCI (3.4 g, 18 mmol, 1.4 eq) and DMAP (0.11 g, 9.91 mmol, 0.07 eq) at room temperature and the resulting solution was stirred for 12 h. The reaction mixture was quenched with 1 N aqueous HCl and the solution was extracted with ethyl acetate (4×50 mL). The combined organic extracts were washed with 10% aqueous LiCl (3×70 mL), dried (Na2SO4), filtered and the filtrate concentrated in vacuo to afford the product (2.5 g, 73%) as a solid, which was used without further purification. 1H NMR (DMSO-d6) δ 8.17–8.20 (m, 1H), 8.03–8.05 (m, 1H), 7.38–7.46 (m, 2H), 7.16–7.22 (m, 2H), 6.37 (dd, 1H, J=6.94 Hz), 5.13 (s, 2H), 3.73 (s, 3H); HRMS(ESI): calcd.: 262.0879, found: 262.0885.

後処理

  1. stirringthe resulting solution was stirred for 12 h
  2. customThe reaction mixture was quenched with 1 N aqueous HCl
  3. extractionthe solution was extracted with ethyl acetate (4×50 mL)
  4. washThe combined organic extracts were washed with 10% aqueous LiCl (3×70 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo

出典と根拠

ORDレコード
ord-606731b10f1b43a985c14dd093935f6a
出典データセット
uspto-grants-2007_02
特許番号
US07173031B2

関連ノート

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