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Aluminium lithium hydride → HCID 59160552, 화합물

HRID 1958670
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HRID 1958670 반응식
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[NH:12][C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=3)=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)[N:15]=2)=[CH:6][C:3]=1[C:4]#[N:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[NH:12][C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=3)=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)[N:15]=2)=[CH:6][C:3]=1[CH2:4][NH2:5]
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참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 44545795HCID 44545795, 화합물

생성물 1

HCID 59160552HCID 59160552, 화합물수율 53%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 2-Fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)benzonitrile (Example 76) (100 mg, 0.238 mmol) in THF (1.5 mL) was added LAH (1M solution in THF, 476 uL, 0.476 mmol) and the mixture was stirred at room temperature for 2 hours. The reaction was quenched by addition of ethyl acetate (1 mL) and H2O (3 drops), and the mixture was stirred for 30 min. The mixture was dried over Na2SO4, filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by MPLC (MeOH:CH2Cl2=1:50 (v/v) to 1:20 (v/v)) to afford the title compound (53.2 mg, 53%). (300 MHz, CDCl3+CD3OD) δ 2.49 (3H, s), 3.87 (2H, s), 4.17 (2H, s), 6.95-7.01 (2H, m), 7.17-7.33 (3H, m), 7.35-7.43 (2H, m), 7.96 (1H, d), 8.08-8.17 (3H, m), 8.91 (1H, dd), 10.40 (1H, bs), MS (ESI) m/z 424 (MH+).

후처리

  1. customThe reaction was quenched by addition of ethyl acetate (1 mL) and H2O (3 drops)
  2. stirringthe mixture was stirred for 30 min
  3. dry with materialThe mixture was dried over Na2SO4
  4. filtrationfiltered through celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by MPLC (MeOH:CH2Cl2=1:50 (v/v) to 1:20 (v/v))

출처 및 근거

ORD 기록
ord-d1c4bd1f8032406485dddedaac9569f2
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08410146B2

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