Sodium Dithionite → HCID 178488891, compound

HRID 416751Notes

Reaction equation

HRID 416751 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(O)C>[Cl:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:14][CH2:13]2)=[C:4]2[N:9]=[C:28]([C:27]3[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 312444-MethoxybenzaldehydeHCID 578972955-Chloro-4-(4-isobutylpiperazin-1-yl)-3-nitropyridin-2-amine

Product 1

HCID 178488891HCID 178488891, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

To a mixture of 5-chloro-4-(4-isobutylpiperazin-1-yl)-3-nitropyridin-2-amine (0.032 g, 0.10 mmol), and ethanol (3.0 ml) was added 4-methoxybenzaldehyde (0.023 g, 0.17 mmol) with the aid of ethanol (1 ml) followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.4 ml, 0.4 mmol). The reaction mixture was heated at 70° C. for 4.5 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 with 40% ethyl acetate in dichloromethane, and then 2.5% methanol in ethyl acetate/dichloromethane (v/v; 1:1). The title compound was obtained as a white solid (0.013 g, 32%); 1H-NMR (500 MHz, DMSO-d6) 0.90 (d, J=6.55 Hz, 6H, CH(CH3)2), 1.83 (m, 1H, CH(CH3)2), 2.12 (d, J=7.39 Hz, 2H, N—CH2), 2.55 (br s, 4H, piperazine N(CH2)2), 3.68 (br s, 4H, piperazine N(CH2)2), 3.84 (s, 3H, OCH3), 7.10 (d, J=8.83 Hz, 2H) and 8.13 (d, J=8.78 Hz, 2H) (3,5-C6H4OMe2 and 2,6-C6H4—OMe), 8.07 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.30 (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 with 40% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-400873913520444f95358a966835e518
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

Loading…