4-(Dimethylamino)Benzaldehyde → (4-(6-Chloro-2-(4-(dimethylamino)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl)piperazin-1-yl)(4-methoxyphenyl)methanone

HRID 416718Notes

Reaction equation

HRID 416718 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[O:18])[CH2:13][CH2:12]2)[C:5]([Cl:27])=[CH:4][N:3]=1.[CH3:28][N:29]([CH3:38])[C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(O)C>[Cl:27][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)=[O:18])[CH2:13][CH2:12]2)=[C:7]2[N:8]=[C:34]([C:33]3[CH:36]=[CH:37][C:30]([N:29]([CH3:38])[CH3:28])=[CH:31][CH:32]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 74794-(Dimethylamino)BenzaldehydeHCID 24489Sodium DithioniteHCID 57897177(4-(2-Amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)(4-methoxyphenyl)methanone

Product 1

HCID 178491576(4-(6-Chloro-2-(4-(dimethylamino)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl)piperazin-1-yl)(4-methoxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of (4-(2-amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)(4-methoxyphenyl)methanone (0.034 g, 0.09 mmol), ethanol (3 ml), and 4-dimethylamino-benzaldehyde (0.018 g, 0.12 mmol) was added a freshly prepared aqueous solution of Na2S2O4 (1M; 0.35 ml, 0.35 mmol). The reaction mixture was heated at 70° C. for 5 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 first with ethyl acetate/dichloromethane (v/v; 6:4) and then 2% methanol in ethyl acetate/dichloromethane (v/v; 1:1). The title compound was isolated as a pale yellow solid after trituration with diethyl ether (0.008 g, 20%); 1H-NMR (500 Mz, DMSO-d6) 3.00 (s, 6H, N(CH3)2), 3.68 (br s), and 3.72 (br s) (8H, piperazine N(CH2)2), 3.81 (s, 3H, OCH3), 6.82 (d, J=8.93 Hz, 2H), and 8.01 (d, J=8.85 Hz, 2H) (2,6-C6H4—NMe2 and 3,5-C6H4—NMe2), 7.02 (d, J=8.64 Hz, 2H) and 7.45 (d, J=8.62 Hz, 2H) (2,6-C6H4—OMe and 3,5-C6H4—OMe), 8.06 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.15 (s, 1H, imidazo[4,5-b]pyridine N—H);

Workup

  1. temperatureto cool to room temperature
  2. customthe solvents were removed in vacuo
  3. customThe residue was absorbed on silica gel
  4. washwas eluted first with ethyl acetate/dichloromethane (v/v; 6:4)

Sources & evidence

ORD record
ord-24978a1b2390488dac02f625d8d921af
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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