4-(Dimethylamino)Benzaldehyde → HCID 178482684, compound

HRID 416755Notes

Reaction equation

HRID 416755 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](=[O:26])[CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:13][CH2:12]2)[C:5]([Br: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>[Br:27][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:26])[CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[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 57897247HCID 57897247, compound

Product 1

HCID 178482684HCID 178482684, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 1-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)-2-phenoxyethanone (0.048 g, 0.11 mmol), and ethanol (4.0 ml) was added 4-dimethylaminobenzaldehyde (0.021 g, 0.14 mmol) 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 concentrated in vacuo. The residue was triturated with water, the precipitate was collected by filtration, washed with water, ethanol, and diethyl ether to afford the title compound as a pale yellow solid (0.027 g, 46%); 1H-NMR (500 MHz, DMSO-d6) 3.00 (s, 6H, N(CH3)2), 3.58 (br s) and 3.70 (br s) (8H, 2× piperazine N(CH2)2), 4.92 (s, 2H, COCH2O), 6.95 (m, 3H) and 7.30 (m, 2H) (ArH), 6.82 (d, J=9.02 Hz, 2H) and 8.02 (d, J=8.92 Hz, 2H) (3,5-C6H4NMe2 and 2,6-C6H4—NMe2), 8.19 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.23 (s, 1H, imidazo[4,5-b]pyridine N—H);

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with water
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water, ethanol, and diethyl ether

Sources & evidence

ORD record
ord-507617eaf5fb41749ca0e459e4bcd075
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

Loading…