4-(Dimethylamino)Benzaldehyde → HCID 178482677, compound

HRID 416731Notes

Reaction equation

HRID 416731 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[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)=[O:19])[CH2:13][CH2:12]2)[C:5]([Cl:28])=[CH:4][N:3]=1.[CH3:29][N:30]([CH3:39])[C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(O)C>[Cl:28][C:5]1[C:6]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)=[O:19])[CH2:15][CH2:16]2)=[C:7]2[N:8]=[C:35]([C:34]3[CH:37]=[CH:38][C:31]([N:30]([CH3:39])[CH3:29])=[CH:32][CH:33]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 74794-(Dimethylamino)BenzaldehydeHCID 24489Sodium DithioniteHCID 46868216HCID 46868216, compound

Product 1

HCID 178482677HCID 178482677, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 2-(4-(2-amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)-N-(3-chlorophenyl)acetamide (0.036 g, 0.08 mmol), ethanol (3.5 ml), and 4-dimethylaminobenzaldehyde (0.017 g, 0.11 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 3 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 30% ethyl acetate in dichloromethane and then 1.5% methanol in ethyl acetate/dichloromethane (v/v; 1:1). The title compound was obtained as a pale yellow solid after trituration with diethyl ether (0.004 g, 7%); 1H-NMR (500 MHz, DMSO-d6) 2.78 (br s, 4H, piperazine N(CH2)2), 3.00 (s, 6H, N(CH3)2), 3.24 (s, 2H, NCH2CO), 3.76 (br s, 4H, piperazine N(CH2)2), 6.82 (d, J=8.96 Hz, 2H) and 8.01 (d, J=8.91 Hz, 2H) (3,5-C6H4NMe2 and 2,6-C6H4—NMe2), 7.12 (d, J=7.62 Hz, 1H) and 7.60 (d, J=9.25 Hz, 1H) (4-ArH and 6-ArH), 7.34 (t, J=6.85 Hz, 1H, 5-ArH), 7.90 (s, 1H, 2-ArH), 8.03 (s, 1H, imidazo[4,5-b]pyridine 5-H), 9.96 (s, 1H, CONH), 13.09 (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 30% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-cdd7d44b289a4c4f95aa1d137d62d405
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

Loading…