HCID 178451735, 화합물 → Tert-butyl 5-(1-(tert-butoxycarbonyl)piperidin-4-yl)-3-iodo-1h-indazole-1-carboxylate

HRID 1520018노트

반응식

HRID 1520018 반응식
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[CH:9]=2)[NH:4][N:3]=1>C(#N)C>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][CH:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[N:3]=[C:2]3[I:1])[CH2:12][CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

참가 물질

3

반응물 1

HCID 178451735HCID 178451735, 화합물

생성물 1

HCID 67981049Tert-butyl 5-(1-(tert-butoxycarbonyl)piperidin-4-yl)-3-iodo-1h-indazole-1-carboxylate수율 148.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of tert-butyl 4-(3-iodo-1H-indazol-5-yl)piperidine-1-carboxylate (218. mg; 0.51 mmol; 1.0 eq.), di-tert-butyldicarboxylate (145 mg; 0.66 mmol; 1.3 eq.), diméthylamino-4-pyridine (12.5 mg; 0.10 mmol; 0.20 eq.) and TEA (86.0 μl; 0.61 mmol; 1.2 eq.) in acetonitrile (6.5 mL) was stirred at RT O/N. Acetonitrile was removed under reduced pressure, the residue was diluted with water and extracted three times with Ether. Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude was purified by flash chromatography on silica (heptane/EtOAc, gradient from 90:10 to 75:25) to give the title compound as a colorless oil (200 mg, 74%). 1H NMR (300 MHz, DMSO-d6) δ 7.99 (d, J=8.7 Hz, 1H), 7.62 (dd, J=1.6, 8.7 Hz, 1H), 7.35 (s, 1H), 4.18-4.03 (m, 2H), 2.96-2.73 (m, 3H), 1.87-1.75 (m, 2H), 1.64 (s, 9H). 1.61-1.48 (m, 2H), 1.42 (s, 9H). (Condition A): Rt 6.33 min (purity 99.8%).

후처리

  1. customAcetonitrile was removed under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted three times with Ether
  4. washCombined organic phases were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was purified by flash chromatography on silica (heptane/EtOAc, gradient from 90:10 to 75:25)

출처 및 근거

ORD 기록
ord-16a6b0ba1a0442c394c26ce5030eabf1
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073892B2

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