HCID 57546118, 화합물 → HCID 57546152, 화합물

HRID 913920노트

반응식

HRID 913920 반응식
[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([O:16][CH2:17][C:18]2([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[C:12]([O:14][CH3:15])=[O:13])[C:8]2[C:4](=[CH:5][N:6](COCC[Si](C)(C)C)[N:7]=2)[CH:3]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]([O:16][CH2:17][C:18]3([C:31]4[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=4)[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[C:12]([O:14][CH3:15])=[O:13])[CH:10]=1)[NH:7][N:6]=[CH:5]2

참가 물질

3

반응물 1

HCID 57546118HCID 57546118, 화합물

생성물 1

HCID 57546152HCID 57546152, 화합물

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

tert-Butyl 4-((1-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)-2-methoxy-2-oxoethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate (25 mg) was stirred in trifluoroacetic acid (50% in dichloromethane, 1.5 mL) for 4 h and concentrated. The residue was loaded onto a strong cation exchange cartridge and washed with several volumes of methanol. The product was eluted with 2M ammonia in methanol and concentrated. The crude piperidine was dissolved in dichloromethane (1 mL) and treated with di-tert-butyldicarbonate (17 mg). After 15 min, the reaction was quenched by addition of 2 M ammonia in methanol and concentrated. Column chromatography (ethyl acetate/n-hexane) gave the title compound. 1H-NMR (CDCl3, 500 MHz) δ 10.14 (bs, 1H), 7.93 (s, 1H), 7.66 (d, J=1.8, 1H), 7.29 (dd, J=8.2, 5.2, 2H), 7.07 (dd, J=8.9, 8.5, 2H), 4.85 (s, 1H), 3.50-3.80 (m, 6H), 3.36 (d, J=8.5, 1H), 3.02 (m, 2H), 2.15 (m, 2H), 1.81 (m, 2H), 1.42 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 169.8, 161.7 (d, J=247 Hz), 155.0, 137.82, 137.79, 136.0, 133.7, 128.8 (d, J=7.7 Hz), 126.2, 126.1, 125.0, 120.8, 119.5, 115.7 (d,J=21 Hz), 80.7, 79.6, 79.0, 52.7, 41.3, 39.9 (br), 32.3, 32.2, 28.5.

후처리

  1. concentrationconcentrated
  2. washwashed with several volumes of methanol
  3. washThe product was eluted with 2M ammonia in methanol
  4. concentrationconcentrated
  5. dissolutionThe crude piperidine was dissolved in dichloromethane (1 mL)
  6. additiontreated with di-tert-butyldicarbonate (17 mg)
  7. customthe reaction was quenched by addition of 2 M ammonia in methanol
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ea8bd8bdffd149d885188a4147be1694
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

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