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

HRID 2422538노트

반응식

HRID 2422538 반응식
[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]

참가 물질

7

반응물 3

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

생성물 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

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8dc0034b807946dcacd09bd7f1c9a81e
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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