Benzaldehyde → 2-[4-(6-Chloro-2-phenyl-3H-imidazo[4,5-b]pyridin-7-yl)-piperazin-1-yl]-N-thiazol-2-yl-acetamide

HRID 416701

反応式

HRID 416701 の反応式
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([NH:20][C:21]3[S:22][CH:23]=[CH:24][N:25]=3)=[O:19])[CH2:13][CH2:12]2)[C:5]([Cl:26])=[CH:4][N:3]=1.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C>[Cl:26][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([NH:20][C:21]3[S:22][CH:23]=[CH:24][N:25]=3)=[O:19])[CH2:13][CH2:12]2)=[C:7]2[N:8]=[C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:1][C:2]2=[N:3][CH:4]=1

参加物

5

反応物 3

HCID 240BenzaldehydeHCID 24489Sodium DithioniteHCID 468678042-(4-(2-amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide

生成物 1

HCID 1785212042-[4-(6-Chloro-2-phenyl-3H-imidazo[4,5-b]pyridin-7-yl)-piperazin-1-yl]-N-thiazol-2-yl-acetamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

To a mixture of 2-[4-(2-amino-5-chloro-3-nitro-pyridin-4-yl)-piperazin-1-yl]-N-thiazol-2-yl-acetamide (0.040 g, 0.10 mmol), ethanol (3 ml), and benzaldehyde (0.015 g, 0.14 mmol) was added a freshly prepared aqueous solution of sodium dithionite (Na2S2O4) (1M; 0.4 ml, 0.4 mmol). The reaction mixture was heated at 70° C. for 6 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 70% dichloromethane in ethyl acetate and then 2% methanol in ethyl acetate/dichloromethane (v/v; 1:1). The title compound was obtained as an off white solid after trituration with diethyl ether (0.011 g, 24%); 1H-NMR (500 MHz, DMSO-d6) 2.73 (br s, 4H, piperazine N(CH2)2), 3.40 (s, 2H, CH2CO), 3.75 (br s, 4H, piperazine N(CH2)2), 7.23 (d, J=3.46 Hz, 1H) and 7.49 (d, J=3.46 Hz, 1H) (thiazole 4-H, 5-H), 8.12 (s, 1H, imidazo[4,5-b]pyridine 5-H), 7.60 (m, 3H) and 8.19 (d, J=7.00 Hz, 2H) (ArH), 11.92 (s, 1H, CONH), 13.49 (s, 1H, imidazo[4,5-b]pyridine N—H); LC-MS (ESI, m/z) Rt=6.16 min—454, 456 [(M+H)+, Cl isotopic pattern]. ESI-HRMS: Found: 454.1230, calculated for C21H21N7OSCl (M+H)+: 454.1217.

後処理

  1. temperatureto cool to room temperature
  2. customthe solvents were removed in vacuo
  3. customThe residue was absorbed on silica gel
  4. washwas eluted with 70% dichloromethane in ethyl acetate

出典と根拠

ORDレコード
ord-40c4f86020554d9ebfd5b07c8e12fc3a
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

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