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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
ノート
印刷プレビュー

反応式

HRID 2099828 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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)+.

後処理

  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%)

出典と根拠

ORDレコード
ord-1980e7ebc94d42ebae551b2def1c64c9
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07569578B2

反応ノート

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