Ethanol → 2-(4-((1H-Pyrazol-1-yl)methyl)phenyl)-6-bromo-7-(4-((1-methyl-1H-imidazol-5-yl)methyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridine

HRID 416945ノート

反応式

HRID 416945 の反応式
[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[N:23]([CH3:24])[CH:22]=[N:21][CH:20]=3)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.CCO.[N:28]1([CH2:33][C:34]2[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=2)[CH:32]=[CH:31][CH:30]=[N:29]1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(Cl)Cl.N.CN(C=O)C>[N:28]1([CH2:33][C:34]2[CH:41]=[CH:40][C:37]([C:38]3[NH:8][C:5]4=[N:6][CH:7]=[C:2]([Br:1])[C:3]([N:12]5[CH2:17][CH2:16][N:15]([CH2:18][C:19]6[N:23]([CH3:24])[CH:22]=[N:21][CH:20]=6)[CH2:14][CH2:13]5)=[C:4]4[N:9]=3)=[CH:36][CH:35]=2)[CH:32]=[CH:31][CH:30]=[N:29]1

参加物

8

反応物 4

HCID 702EthanolHCID 24489Sodium DithioniteHCID 185258764-(1H-Pyrazol-1-ylmethyl)benzaldehydeHCID 578972865-Bromo-4-(4-((1-methyl-1H-imidazol-5-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine

生成物 1

HCID 1784812402-(4-((1H-Pyrazol-1-yl)methyl)phenyl)-6-bromo-7-(4-((1-methyl-1H-imidazol-5-yl)methyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridine

試薬・触媒・溶媒 3

HCID 222Ammonia触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
85 °C

実験手順

To a mixture of 5-bromo-4-(4-((1-methyl-1H-imidazol-5-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine (0.050 g, 0.126 mmol, 1 eq), EtOH (2.2 mL), and DMF (0.3 mL), 4-(1H-pyrazol-1-ylmethyl)-benzaldehyde (0.026 g, 0.14 mmol, 1.1 eq) was added followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.38 mL, 0.38 mmol). The reaction mixture was heated at 85° C. for 24 h, then allowed to cool to room temperature and diluted with DCM and a few drops of aqueous NH3 until complete dissolution was observed. This solution was deposited on two preparative silica TLC plates and eluted with DCM/MeOH (v/v; 92:8). The title compound was obtained as a solid after trituration with diethyl ether (0.008 g, 12%); 1H-NMR (500 Mz, DMSO-d6): 2.55-2.62 (m, 4H, piperazine N(CH2)2), 3.53 (s, 2H, NCH2), 3.61-3.67 (m, 4H, piperazine N(CH2)2), 3.68 (s, 3H, imidazole Me), 5.41 (s, 2H, NCH2), 6.30 (t, J=2.0 Hz, 1H, pyrazole H-4), 6.81 (s, 1H, imidazole H-4), 7.34 (d, J=8.0 Hz, 2H, ArH, C6H4), 7.49 (d, J=1.5 Hz, 1H, pyrazole H-3), 7.58 (s, 1H, imidazole 2-H), 7.85 (d, J=2.0 Hz, 1H, pyrazole H-3), 8.13 (d, J=8.5 Hz, 2H, ArH, C6H4), 8.23 (s, 1H, imidazo[4,5-b]pyridine 5-H); LC (Method B)-MS (ESI, m/z) 2.71 min—532/534 [(M+H)+], Br isotopic pattern]. ESI-HRMS: Found: 532.1567, calculated for C25H27BrN9 (M+H)+: 532.1573.

後処理

  1. additionwas added
  2. temperatureto cool to room temperature
  3. washeluted with DCM/MeOH (v/v; 92:8)

出典と根拠

ORDレコード
ord-da11842a7321405690894d525c431b24
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

反応ノート

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