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

HRID 749441노트

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HRID 749441 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 689772612-(4-fluorophenyl)-N-methylpent-4-enamide수율 78.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-007169fc74734a77aee59a9efc90c533
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402581B2

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