Sodium Dithionite → HCID 178488868, compound

HRID 416745Notes

Reaction equation

HRID 416745 reaction equation
[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][CH:22]=[CH:21][N:20]=3)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=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][CH:22]=[CH:21][N:20]=3)[CH2:14][CH2:13]2)=[C:4]2[N:9]=[C:31]([C:30]3[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 312444-MethoxybenzaldehydeHCID 578972385-Bromo-3-nitro-4-(4-(pyridin-2-ylmethyl)piperazin-1-yl)pyridin-2-amine

Product 1

HCID 178488868HCID 178488868, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

To a mixture of 5-bromo-3-nitro-4-(4-(pyridin-2-ylmethyl)piperazin-1-yl)pyridin-2-amine (0.043 g, 0.11 mmol), and ethanol (2.5 ml) was added 4-methoxybenzaldehyde (0.024 g, 0.18 mmol) with the aid of ethanol (1 ml) followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.44 ml, 0.44 mmol). The reaction mixture was heated at 70° C. for 4 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 ethyl acetate/dichloromethane (v/v; 1:1), and then 4% methanol in ethyl acetate/dichloromethane (v/v; 1:1). The title compound was obtained as a yellow solid after trituration with diethyl ether (0.010 g, 19%); 1H-NMR (500 MHz, DMSO-d6) 2.67 (br s, 4H, piperazine N(CH2)2), 3.68 (br s, 4H, piperazine N(CH2)2), 3.70 (s, 2H, NCH2), 3.84 (s, 3H, OMe), 7.10 (d, J=8.86 Hz, 2H) and 8.13 (d, J=8.75 Hz, 2H) (3,5-C6H4OMe and 2,6-C6H4—OMe), 7.28 (dd, J=5.00, 6.45 Hz, 1H), 7.52 (d, J=7.80 Hz, 1H), 7.79 (td, J=1.75, 7.65 Hz, 1H) and 8.52 (d, J=4.80 Hz, 1H) (pyrid-2-yl protons), 8.20 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.35 (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 ethyl acetate/dichloromethane (v/v; 1:1)

Sources & evidence

ORD record
ord-19d965a4f8044fc5b8a4472f42b3efa7
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

Loading…