Ethanol → 6-Bromo-7-[4-(4-Chlorobenzyl)piperazin-1-Yl]-2-[4-(Morpholin-4-Ylmethyl)phenyl]-3h-Imidazo[4,5-B]pyridine

HRID 416797노트

반응식

HRID 416797 반응식
[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH: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:29]1([CH2:35][C:36]2[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][CH:37]=2)[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(OCC)C>[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)=[C:4]2[N:9]=[C:40]([C:39]3[CH:38]=[CH:37][C:36]([CH2:35][N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[CH:43][CH:42]=3)[NH:8][C:5]2=[N:6][CH:7]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 24489Sodium DithioniteHCID 27954984-[(Morpholin-4-yl)methyl]benzaldehydeHCID 468687815-Bromo-4-(4-(4-chlorobenzyl)piperazin-1-yl)-3-nitropyridin-2-amine

생성물 1

HCID 1784781316-Bromo-7-[4-(4-Chlorobenzyl)piperazin-1-Yl]-2-[4-(Morpholin-4-Ylmethyl)phenyl]-3h-Imidazo[4,5-B]pyridine

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
70 °C

실험 절차

To a mixture of 5-bromo-4-[4-(4-chloro-benzyl)-piperazin-1-yl]-3-nitro-pyridin-2-ylamine (0.064 g, 0.15 mmol) and EtOH (6.5 ml) was added 4-morpholin-4-ylmethyl-benzaldehyde (0.038 g, 0.18 mmol) followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.60 ml, 0.60 mmol). The reaction mixture was stirred at 70° C. for 9 h, then allowed to cool to room temperature and concentrated in vacuo. The residue was absorbed on silica gel, the free-running powder was placed on a 10 g isolute silica column and elution with a gradient of methanol (0 to 9%) in ethyl acetate/dichloromethane (v:v; 1:1) afforded a yellow solid. The title compound was obtained as a pale yellow solid after trituration with diethyl ether (0.003 g, 3%). 1H-NMR (500 MHz, DMSO-d6) 2.38 (br s, 4H) and 3.59 (t, J=4.5 Hz, 4H) (morpholine N(CH2)2 and morpholine O(CH2)2), 2.61 (br s, 4H, piperazine N(CH2)2), 3.66 (br s, 4H, piperazine N(CH2)2), 3.54 (s, 2H) and 3.57 (s, 2H) (NCH2—C6H4Cl and C6H4CH2), 7.41 (m, 4H, C6H4Cl), 7.47 (d, J=8.2 Hz, 2H) and 8.14 (d, J=8.2 Hz, 2H) (3,5-C6H4 and 2,6-C6H4), 8.23 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.48 (br s, 1H, imidazo[4,5-b]pyridine N—H);

후처리

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was absorbed on silica gel
  4. washthe free-running powder was placed on a 10 g isolute silica column and elution with a gradient of methanol (0 to 9%) in ethyl acetate/dichloromethane (v:v; 1:1)
  5. customafforded a yellow solid

출처 및 근거

ORD 기록
ord-bd3123511314452192458c4657badc46
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088761B2

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