Perfluoro-1-butanesulfonyl fluoride → HCID 57545990, 화합물

HRID 913932노트

반응식

HRID 913932 반응식
[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([O:14][CH2:15][C:16]2([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:12]O)[C:8]2[C:4](=[CH:5][N:6]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[N:7]=2)[CH:3]=1.C(N(C(C)C)CC)(C)C.F.F.F.C(N(C(C)C)CC)(C)C.[F:65]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.C(=O)(O)[O-].[Na+]>C(#N)C.C(OCC)C>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([O:14][CH2:15][C:16]2([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:18][CH2:17]2)[CH2:12][F:65])[C:8]2[C:4](=[CH:5][N:6]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:42])([CH3:43])[CH3:41])[N:7]=2)[CH:3]=1

참가 물질

8

반응물 5

HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 45108321N-Ethyl-N-(propan-2-yl)propan-2-amine--hydrogen fluoride (1/3)HCID 57545941HCID 57545941, 화합물

생성물 1

HCID 57545990HCID 57545990, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

실험 절차

To a solution of tert-butyl 4-((1-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)-2-hydroxyethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate (50 mg, 0.079 mmol) in acetonitrile (0.1 mL) at room temperature was added diisopropylethylamine (0.062 mL, 0.355 mmol), diisopropylethylamine trihydrofluoride (22.4 mg, 0.118 mmol), and perfluoro-1-butanesulfonyl fluoride (0.028 mL, 0.16 mmol). The reaction was stirred at room temperature overnight. The reaction was poured into saturated sodium bicarbonate, and diluted with diethyl ether. The ethereal was washed with water, then brine, dried over magnesium sulfate, and concentrated. Column chromatography (15%→20% ethyl acetate/n-hexane) gave 40 mg (80%) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 8.01 (s, 1H), 7.54 (d, J=1.8 Hz, 1H), 7.33 (dd, J=9.2, 5.5 Hz, 2H), 7.03 (dd, J=8.9, 8.5 Hz, 2H), 6.73 (bs, 1H), 5.66 (d, J=10.7 Hz, 1H), 5.63 (d, J=10.7 Hz, 1H), 5.16 (m, 1H), 4.62 (ddd, J=46.7, 9.5, 2.4 Hz, 1H), 4.42 (ddd, J=48.2, 9.8, 7.3 Hz, 1H), 3.75 (bs, 2H), 3.60 (m, 2H), 3.52 (d, J=9.2 Hz, 1H), 3.45 (d, J=9.2 Hz, 1H), 3.10 (bs, 1H), 3.03 (m, 1H), 2.27 (m, 1H), 2.07 (m, 1H), 1.99 (m, 1H), 1.87 (m, 1H), 1.44 (s, 9H), 0.92 (m, 2H), −0.05 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 161.5 (d, J=246 Hz), 155.1, 145.4, 138.5, 128.9 (d, J=7.7 Hz), 128.2, 128.11, 128.07, 124.9, 122.7, 122.6, 118.9, 115.3 (d, J=21 Hz), 85.9, 84.4, 81.9, 79.5, 78.8, 77.3, 77.1, 67.8, 41.5, 40.5, 39.7, 32.2, 31.8, 28.6, 17.9, −1.4. Mass spec.: 636.43 (MH)+.

후처리

  1. washThe ethereal was washed with water
  2. dry with materialbrine, dried over magnesium sulfate
  3. concentrationconcentrated
  4. customColumn chromatography (15%→20% ethyl acetate/n-hexane) gave 40 mg (80%) as a colorless film

출처 및 근거

ORD 기록
ord-45ec5189f3a34364b7da5ce72d3853d6
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

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