Sodium Dithionite → 2-(4-(6-Chloro-2-(4-methoxyphenyl)-3H-imidazo[4,5-b]pyridin-7-yl)piperazin-1-yl)-N-(3-methylisoxazol-5-yl)acetamide

HRID 416792Notes

Reaction equation

HRID 416792 reaction equation
[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[O:25][N:24]=[C:23]([CH3:26])[CH:22]=3)=[O:19])[CH2:13][CH2:12]2)[C:5]([Cl:27])=[CH:4][N:3]=1.[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(O)C>[Cl:27][C:5]1[C:6]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][C:18]([NH:20][C:21]3[O:25][N:24]=[C:23]([CH3:26])[CH:22]=3)=[O:19])[CH2:15][CH2:16]2)=[C:7]2[N:8]=[C:28]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 312444-MethoxybenzaldehydeHCID 57897277HCID 57897277, compound

Product 1

HCID 1784888922-(4-(6-Chloro-2-(4-methoxyphenyl)-3H-imidazo[4,5-b]pyridin-7-yl)piperazin-1-yl)-N-(3-methylisoxazol-5-yl)acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

To a mixture of 2-(4-(2-amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)-N-(3-methylisoxazol-5-yl)acetamide (0.036 g, 0.09 mmol) and ethanol (3 ml) was added p-anisaldehyde (0.024 g, 0.18 mmol) with the aid of ethanol (1 ml) followed by a freshly prepared 1M aqueous solution of Na2S2O4 (0.36 ml, 0.36 mmol). The reaction mixture was stirred at 70° C. for 6.5 h, then allowed to cool to room temperature and concentrated in vacuo. The residue was absorbed on silica gel, and the free-running powder was placed on a 10 g silica isolute column which was eluted with ethyl acetate/dichloromethane (v/v; 1:1), and 2% methanol in ethyl acetate/dichloromethane (v/v; 1:1). The title compound was obtained as a pale yellow solid after trituration with diethyl ether (0.008 g, 18%). 1H-NMR (500 MHz, DMSO-d6) 2.19 (s, 3H, isoxazole CH3), 2.73 (s, 4H, piperazine N(CH2)2), 3.32 (s, 2H, NCH2CO), 3.73 (s, 4H, piperazine N(CH2)2), 3.83 (s, 3H, OCH3), 6.18 (s, 1H, isoxazole C—H), 7.11 (d, J=8.9 Hz, 2H) and 8.13 (d, J=8.8 Hz, 2H) (3,5-C6H4OMe and 2,6-C6H4OMe), 8.09 (s, 1H, imidazo[4,5-b]pyridine 5-H), 11.43 (br s, 1H, CONH), 13.38 (br s, 1H, imidazo[4,5-b]pyridine N—H);

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was absorbed on silica gel
  4. washwas eluted with ethyl acetate/dichloromethane (v/v; 1:1), and 2% methanol in ethyl acetate/dichloromethane (v/v; 1:1)

Sources & evidence

ORD record
ord-2072ba3ec012494389b94ba057c0e083
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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