Methylamine → 2-(4-fluorophenyl)-N-methylpent-4-enamide

HRID 749441ノート

反応式

HRID 749441 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH:13]=[CH2:14])[C:9](O)=[O:10])=[CH:4][CH:3]=1.[CH3:15][N:16](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH:13]=[CH2:14])[C:9]([NH:16][CH3:15])=[O:10])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 183545112-(4-Fluorophenyl)pent-4-enoic acid

生成物 1

HCID 689772612-(4-fluorophenyl)-N-methylpent-4-enamide収率 78.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

2-(4-Fluorophenyl)pent-4-enoic acid (Bioorg. Med. Chem. Lett. 2000, 1893; 4.20 g, 21.6 mmol) was dissolved in CH2Cl2 (75 mL) and to the resultant solution was added TBTU (7.29 g, 22.7 mmol). The mixture was stirred at RT for 15 min and then methylamine (11.9 mL of 2M THF solution, 23.8 mmol) and DIPEA (11.2 g, 86.5 mmol) were added. The reaction mixture was stirred at room temperature for 3 h, subsequently diluted with CH2Cl2 (50 mL) and then washed several times with water. The solvent was removed by evaporation and the residue flash chromatographed on silica gel (heptane-ethyl acetate, 1:1). There was obtained 3.5 g (78%) of 2-(4-fluorophenyl)-N-methylpent-4-enamide as an oil, which shortly after crystallized. 1H NMR (400 MHz, CDCl3): 2.5 (qn, 1H), 2.7 (d, 3H), 2.9 (qn, 1H), 3.4 (t, 1H), 4.9-5.1 (m, 2H), 5.6-5.8 (m, 1H), 6.0-6.2 (b, 1H), 7.0 (m, 2H), 7.3 (m, 2H).

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 3 h
  2. washwashed several times with water
  3. customThe solvent was removed by evaporation
  4. customthe residue flash chromatographed on silica gel (heptane-ethyl acetate, 1:1)

出典と根拠

ORDレコード
ord-007169fc74734a77aee59a9efc90c533
出典データセット
uspto-grants-2008_07
特許番号
US07402581B2

反応ノート

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