Sodium Dithionite → HCID 178419446、化合物

HRID 416816

反応式

HRID 416816 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[CH:24]=[CH:23][N:22]=[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.[N:25]1([CH2:31][CH2:32][O:33][C:34]2[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=2)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(O)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][N:22]=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)=[C:4]2[N:9]=[C:38]([C:37]3[CH:40]=[CH:41][C:34]([O:33][CH2:32][CH2:31][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[CH:35][CH:36]=3)[NH:8][C:5]2=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 24489Sodium DithioniteHCID 37199024-(2-Morpholinoethoxy)benzaldehydeHCID 468683515-Bromo-3-nitro-4-(4-(pyridin-4-ylmethyl)piperazin-1-yl)pyridin-2-amine

生成物 1

HCID 178419446HCID 178419446、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
80 °C

実験手順

To a mixture of 5-bromo-3-nitro-4-(4-pyridin-4-ylmethyl-piperazin-1-yl)-pyridin-2-ylamine (0.040 g, 0.10 mmol) and EtOH (3.0 ml) was added 4-(2-morpholin-4-yl-ethoxy)-benzaldehyde (0.031 g, 0.13 mmol) with the aid of ethanol (1 ml) followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.40 ml, 0.40 mmol). The reaction mixture was stirred at 80° C. for 20 h, then allowed to cool to room temperature and concentrated in vacuo. The resulting residue was absorbed on silica, and the free-running powder was placed on a 10 g isolute silica column. Elution with a gradient of methanol (0 to 10%) in ethyl acetate/dichloromethane (v:v; 1:1). afforded a pale yellow solid. This material was triturated with diethyl ether, and the resulting white precipitate was collected by filtration, and successively washed with diethyl ether, water, and diethyl ether, then dried in vacuo (0.014 g, 24%); 1H-NMR (500 MHz, DMSO-d6) 2.63 (br s, 4H, piperazine N(CH2)2), 2.72 (t, J=5.7 Hz, 2H, OCH2CH2N), 3.59 (t, J=4.7 Hz, 4H, morpholine O(CH2)2), 3.62, (s, 2H, NCH2-pyridyl), 3.68 (br t, 4H, piperazine N(CH2)2), 4.18 (t, J=5.8 Hz, 2H, OCH2CH2N), 7.11 (d, J=8.9 Hz, 2H) and 8.12 (d, J=8.9 Hz, 2H) (3,5-C6H4— and 2,6-C6H4—), 7.39 (d, J=5.9 Hz, 2H, pyridine 3-H, 5-H), 8.20 (s, 1H, imidazo[4,5-b]pyridine 5-H), 8.54 (d, J=5.9 Hz, 2H, pyridine 2-H, 6-H), 13.34 (br s, 1H, imidazo[4,5-b]pyridine N—H);

後処理

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was absorbed on silica
  4. washElution with a gradient of methanol (0 to 10%) in ethyl acetate/dichloromethane (v:v; 1:1)
  5. customafforded a pale yellow solid
  6. customThis material was triturated with diethyl ether
  7. filtrationthe resulting white precipitate was collected by filtration
  8. washsuccessively washed with diethyl ether, water, and diethyl ether
  9. customdried in vacuo (0.014 g, 24%)

出典と根拠

ORDレコード
ord-72165114f80947b7a737da319da9578a
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

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