Phenylacetylene → HCID 24957856, 화합물

HRID 2381825노트

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HRID 2381825 반응식
[N:1]([C:4]1[S:5][C:6]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])=[C:7]([CH3:9])[N:8]=1)=[N+:2]=[N-:3].C(N(CC)C(C)C)(C)C.[C:29]1([C:35]#[CH:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1.[Cu]I>[CH2:13]([NH:12][C:10]([C:6]1[S:5][C:4]([N:1]2[CH:36]=[C:35]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:3]=[N:2]2)=[N:8][C:7]=1[CH3:9])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 3

HCID 10821PhenylacetyleneHCID 81531DiisopropylethylamineHCID 73213267HCID 73213267, 화합물

생성물 1

HCID 24957856HCID 24957856, 화합물수율 70%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-azido-N-benzyl-4-methylthiazole-5-carboxamide (0.65 g, 2.38 mmol) in tetrahydrofuran (10 mL) was added copper(I) iodide (0.45 g, 2.38 mmol), N,N-diisopropylethylamine (1.24 mL, 7.14 mmol) and phenylacetylene (0.37 g, 3.57 mmol). The reaction mixture was stirred at ambient temperature for 18 hours and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate:petroleum ether, 1:1) to afford the title compound as a white solid in 70% yield: mp 175-178° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.60 (s, 1H), 7.90 (d, J=9.0 Hz, 2H), 7.47-7.37 (m, 8H), 6.11 (br s, 1H), 4.64 (d, J=6.0 Hz, 2H), 2.72 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 160.9, 155.4, 153.3, 148.7, 137.4, 129.2, 129.0, 128.9, 128.8, 127.8, 126.0, 124.4, 116.7, 44.3, 17.4; MS (ES+) m/z 376.3 (M+1).

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (ethyl acetate:petroleum ether, 1:1)

출처 및 근거

ORD 기록
ord-6d7db80d59614b39bcc4c4c5ad052262
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258160B2

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