Ethanol → HCID 178488878, 화합물

HRID 416920노트

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HRID 416920 반응식
[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.[CH:28](=O)[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(Cl)Cl.N.CN(C=O)C>[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]2[N:9]=[C:28]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[NH:8][C:5]2=[N:6][CH:7]=1

참가 물질

8

반응물 4

HCID 702EthanolHCID 24489Sodium DithioniteHCID 312444-MethoxybenzaldehydeHCID 578972865-Bromo-4-(4-((1-methyl-1H-imidazol-5-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine

생성물 1

HCID 178488878HCID 178488878, 화합물

시약·촉매·용매 3

HCID 222Ammonia촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
85 °C

실험 절차

To a mixture of 5-bromo-4-(4-((1-methyl-1H-imidazol-5-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine (0.030 g, 0.076 mmol, 1 eq), EtOH (1.95 mL) and DMF (0.29 mL), p-anisaldehyde (0.011 g, 0.083 mmol, 1.1 eq) was added followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.23 mL, 0.23 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 aq NH3 until complete dissolution was observed. This solution was deposited on two preparative silica TLC plates and eluted with DCM/MeOH (v/v; 94:6). The title compound was obtained as a solid after trituration with diethyl ether (0.009 g, 23%); 1H-NMR (500 Mz, DMSO-d6): δ 2.55-2.62 (m, 4H, piperazine N(CH2)2), 3.54 (s, 2H, NCH2), 3.60-3.66 (m, 4H, piperazine N(CH2)2), 3.68 (s, 3H, imidazole Me), 3.84 (s, 3H, OMe), 6.80 (s, 1H, imidazole 4-H), 7.09 (d, J=9.0 Hz, 2H, ArH, C6H4), 7.57 (s, 1H, imidazole 2-H), 8.13 (d, J=9.0 Hz, 2H, ArH, C6H4), 8.20 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.35 (br s, 1H, imidazo[4,5-b]pyridine N—H); LC (Method B)-MS (ESI, m/z): Rt=2.78 min—482/484 [(M+H+), Br isotopic pattern, 100%]. ESI-HRMS: Found: 482.1295, calculated for C22H25BrN7O (M+H)+: 482.1304.

후처리

  1. additionwas added
  2. temperatureto cool to room temperature
  3. washeluted with DCM/MeOH (v/v; 94:6)

출처 및 근거

ORD 기록
ord-4731bce0136f4f7caab86116d0c622b5
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088761B2

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