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Triethylamine → N-[2-(4-Chlorophenyl)-3-isopropyl-imidazol-4-yl]-2-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]propanamide

HRID 1754389
ノート
印刷プレビュー

反応式

HRID 1754389 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH3:15])[CH3:14])[C:11]([NH2:16])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:17][C:18]1[N:19]([CH:27]([CH3:31])[C:28](O)=[O:29])[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[N:22]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH:13]([CH3:14])[CH3:15])[C:11]([NH:16][C:28](=[O:29])[CH:27]([N:19]3[CH:20]=[C:21]([C:23]([F:24])([F:26])[F:25])[N:22]=[C:18]3[CH3:17])[CH3:31])=[CH:10][N:9]=2)=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867116772-[2-Methyl-4-(trifluoromethyl)imidazol-1-yl]propanoic acidHCID 867243902-(4-Chlorophenyl)-3-isopropyl-imidazol-4-amine

生成物 1

HCID 86724389
N-[2-(4-Chlorophenyl)-3-isopropyl-imidazol-4-yl]-2-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]propanamide
収率 23.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A mixture of 2-(4-chlorophenyl)-3-isopropyl-imidazol-4-amine (0.10 g, 0.43 mmol), 2-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]propanoic acid (0.09 g, 0.43 mmol), HATU (0.16 g, 0.43 mmol), and Et3N (200 μL, 1.4 mmol) in CH2Cl2 (1 mL) was stirred at room temperature for 30 min. The reaction mixture was then diluted with 10 mL of saturated aqueous NaHCO3 solution and extracted with EtOAc. The organic layer was subsequently washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting crude product was purified by flash chromatography (SiO2, 100% EtOAc-30% MeOH/EtOAc) to afford the titled compound as a white solid (0.046 g, 0.10 mmol, 23% yield). 1H NMR (400 MHz, CDCl3) 7.52 (s, 1H), 7.44 (d, J=8.0 Hz, 2H), 7.32 (d, J=8.0 Hz, 2H), 7.07 (s, 1H), 5.18 (q, J=7.1 Hz, 1H), 4.36 (q, J=7.0 Hz, 1H), 2.42 (s, 3H), 1.78 (d, J=7.1 Hz, 3H), 1.33 (d, J=7.0 Hz, 6H). MS: (ES) m/z calculated for C20H21ClF3N5O [M+H]+ 440.1, found 440.4.

後処理

  1. extractionextracted with EtOAc
  2. washThe organic layer was subsequently washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude product was purified by flash chromatography (SiO2, 100% EtOAc-30% MeOH/EtOAc)

出典と根拠

ORDレコード
ord-b41cdc81473742c9ad4d714d889b7632
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09169248B2

反応ノート

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