Diisopropylethylamine → (S)-1-{1-[(4-chloro-2-cyanoquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate

HRID 2422538ノート

反応式

HRID 2422538 の反応式
[N:1]([CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([Cl:17])=[CH:10][C:11]([C:15]#[N:16])=[N:12]2)=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[N+:18]([C:21]1[CH:38]=[CH:37][C:24]([C:25]([O:27][C:28]([CH2:35][CH3:36])([C:31]([F:34])([F:33])[F:32])[C:29]#[CH:30])=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19].C(N(C(C)C)CC)(C)C>C1COCC1.C(OCC)(=O)C.[Cu](I)I>[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][C@@:28]([C:29]2[N:3]=[N:2][N:1]([CH2:4][C:5]3[CH:14]=[C:13]4[C:8]([C:9]([Cl:17])=[CH:10][C:11]([C:15]#[N:16])=[N:12]4)=[CH:7][CH:6]=3)[CH:30]=2)([C:31]([F:32])([F:33])[F:34])[CH2:35][CH3:36])=[O:26])=[CH:37][CH:38]=1)([O-:20])=[O:19]

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 597748703-(Trifluoromethyl)pent-1-YN-3-YL 4-nitrobenzoateHCID 597748847-(Azidomethyl)-4-chloroquinoline-2-carbonitrile

生成物 1

HCID 66790930(S)-1-{1-[(4-chloro-2-cyanoquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 7-(azidomethyl)-4-chloroquinoline-2-carbonitrile (560 mg, 2.3 mmol) and 1-ethyl-1-(trifluoromethyl)prop-2-yn-1-yl 4-nitrobenzoate (S-isomer, 728 mg, 2.42 mmol) in THF (18 mL) was added diisopropylethylamine (2.0 mL, 11.5 mmol) followed by copper iodide (655 mg, 3.45 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with a sat. sol. of NH4Cl, Brine and dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the resulting crude product was purified by flash chromatography (eluting solvent: 5% acetone in CH2Cl2) to afford the title compound. 1H NMR (400 MHz, acetone-d6): δ 8.55 (s, 1H), 8.45 (d, 2H), 8.37 (d, 1H), 8.30 (d, 2H), 8.22 (s, 1H), 8.07 (s, 1H), 7.90 (d, 1H), 6.05 (s, 2H), 3.05 (m, 1H), 2.85 (m, 1H), 1.15 (t, 3H).

後処理

  1. washwashed with a sat. sol. of NH4Cl, Brine
  2. dry with materialdried over anhydrous MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customthe resulting crude product was purified by flash chromatography (eluting solvent: 5% acetone in CH2Cl2)

出典と根拠

ORDレコード
ord-8dc0034b807946dcacd09bd7f1c9a81e
出典データセット
uspto-grants-2011_06
特許番号
US07960409B2

反応ノート

読み込み中…