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N-(1-(1-((2-Chloro-6-methylpyridin-4-yl)methyl)-1H-imidazol-2-yl)-2-(7-methyl-1H-indazol-5-yl)ethyl)-4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxamide → N-[2-(7-methyl-1H-indazol-5-yl)-1-[1-[(2-methyl-4-pyridinyl)methyl]imidazol-2-yl]ethyl]-4-(2-oxo-1,4-dihydroquinazolin-3-yl)piperidine-1-carboxamide

HRID 2099828
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반응식

HRID 2099828 반응식
Cl[C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH:14]([NH:26][C:27]([N:29]2[CH2:34][CH2:33][CH:32]([N:35]3[CH2:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[NH:37][C:36]3=[O:45])[CH2:31][CH2:30]2)=[O:28])[CH2:15][C:16]2[CH:17]=[C:18]3[C:22](=[C:23]([CH3:25])[CH:24]=2)[NH:21][N:20]=[CH:19]3)[CH:5]=[C:4]([CH3:46])[N:3]=1>CO.[Pd]>[CH3:25][C:23]1[CH:24]=[C:16]([CH2:15][CH:14]([NH:26][C:27]([N:29]2[CH2:30][CH2:31][CH:32]([N:35]3[CH2:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[NH:37][C:36]3=[O:45])[CH2:33][CH2:34]2)=[O:28])[C:10]2[N:9]([CH2:8][C:6]3[CH:7]=[CH:2][N:3]=[C:4]([CH3:46])[CH:5]=3)[CH:13]=[CH:12][N:11]=2)[CH:17]=[C:18]2[C:22]=1[NH:21][N:20]=[CH:19]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 1

HCID 11422298N-(1-(1-((2-Chloro-6-methylpyridin-4-yl)methyl)-1H-imidazol-2-yl)-2-(7-methyl-1H-indazol-5-yl)ethyl)-4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxamide

생성물 1

HCID 11478962N-[2-(7-methyl-1H-indazol-5-yl)-1-[1-[(2-methyl-4-pyridinyl)methyl]imidazol-2-yl]ethyl]-4-(2-oxo-1,4-dihydroquinazolin-3-yl)piperidine-1-carboxamide

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

N-(1-(1-((2-Chloro-6-methylpyridin-4-yl)methyl)-1H-imidazol-2-yl)-2-(7-methyl-1H-indazol-5-yl)ethyl)-4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxamide (15.0 mg, 0.024 mmol) in methanol (1.0 mL) was flushed with nitrogen, and treated with palladium (10% on charcoal, 1.5 mg). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen overnight. After 24 h, the reaction was charged with additional palladium (10% on charcoal, 1.5 mg). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated in vacuo. Column chromatography gave 2.4 mg (17%). 1H-NMR (CD3OD, 500 MHz) δ 1.49-1.63 (m, 4H), 2.32 (s, 3H), 2.43 (s, 3H), 2.69-2.78 (m, 2H), 3.98-4.12 (m, 2H), 5.11-5.24 (m, 3H), 5.39 (d, J=17.1, 1H), 6.55 (d, J=0.9, 1H), 6.72 (s, 1H), 6.80 (d, J=7.9, 1H), 6.85 (s, 1H), 6.97 (dd, J=7.6, 7.3, 1H), 7.06 (s, 1H), 7.10-7.76 (m, 6H), 8.03 (d, J=5.2, 1H). Mass spec.: 604.96 (MH)+.

후처리

  1. customThe flask was flushed with hydrogen
  2. waitAfter 24 h
  3. additionthe reaction was charged with additional palladium (10% on charcoal, 1.5 mg)
  4. customThe flask was flushed with hydrogen
  5. stirringto stir under an atmosphere of hydrogen overnight
  6. customThe reaction was flushed with nitrogen
  7. filtrationfiltered through celite
  8. concentrationconcentrated in vacuo
  9. customColumn chromatography gave 2.4 mg (17%)

출처 및 근거

ORD 기록
ord-1980e7ebc94d42ebae551b2def1c64c9
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07569578B2

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