Diisopropylethylamine → 1-(2-(1-(3,5-Dimethoxyphenyl)ethylamino)-4-fluorophenyl)-2,2,2-trifluoroethanone

HRID 1910532

反応式

HRID 1910532 の反応式
[F:1][C:2]([F:14])([F:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1F)=[O:4].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:25]([NH2:27])[CH3:26])[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:24][O:23][C:21]1[CH:20]=[C:19]([CH:25]([NH:27][C:6]2[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=2[C:3](=[O:4])[C:2]([F:14])([F:13])[F:1])[CH3:26])[CH:18]=[C:17]([O:16][CH3:15])[CH:22]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 135102551-(3,5-Dimethoxyphenyl)ethanamineHCID 247268371-(2,4-Difluorophenyl)-2,2,2-trifluoroethanone

生成物 1

HCID 587072861-(2-(1-(3,5-Dimethoxyphenyl)ethylamino)-4-fluorophenyl)-2,2,2-trifluoroethanone収率 34%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

2,2,2-Trifluoro-1-(2,4-difluorophenyl)ethanone (1.0 g, 4.8 mmol), 1-(3,5-dimethoxyphenyl)ethanamine (0.95 g, 5.2 mmol) and N,N-diisopropylethylamine (1.2 g, 9.6 mmol) were stirred at 60° C. in dry acetonitrile (50 mL) for 16 h. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated and purified by silica chromatography in 20% ethyl acetate in hexanes to collect the title compound (600 mg, 34% yield). 1H NMR (400 MHz, CDCl3): δ 9.27 (s, 1H), 7.79 (t, 1H), 6.44 (s, 2H), 6.35 (m, 2H), 6.23 (d, 1H), 4.48 (m, 1H), 3.77 (s, 6H), 1.61 (d, 3H).

後処理

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated
  5. custompurified by silica chromatography in 20% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-223f25e26844404cade38b3a1780d8b6
出典データセット
uspto-grants-2013_12
特許番号
US08604021B2

関連ノート

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