4-(Dimethylamino)Benzaldehyde → HCID 178482682, compound

HRID 416700Notes

Reaction equation

HRID 416700 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]([N:20]([CH3:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][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]([N:20]([CH3:27])[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=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 578972912-[4-(2-Amino-5-chloro-3-nitro-pyridin-4-yl)-piperazin-1-yl]-N-methyl-N-phenyl-acetamide

Product 1

HCID 178482682HCID 178482682, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 2-[4-(2-amino-5-chloro-3-nitro-pyridin-4-yl)-piperazin-1-yl]-N-methyl-N-phenyl-acetamide (0.037 g, 0.09 mmol), ethanol (3 ml), and 4-dimethylamino-benzaldehyde (0.019 g, 0.13 mmol) was added a freshly prepared aqueous solution of Na2S2O4 (1M; 0.4 ml, 0.4 mmol). The reaction mixture was heated at 70° C. for 6 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; 1:1), and then 1-2% methanol in ethyl acetate/dichloromethane (v/v; 1:1). The title compound was obtained after trituration with diethyl ether as a pale yellow solid (0.008 g, 18%); 1H-NMR (500 Mz, DMSO-d6) 2.58 (br s, 4H, piperazine N(CH2)2), 3.00 (s, 6H, N(CH3)2), 3.21 (s, 3H, NCH3), 3.61 (br s, 4H, piperazine N(CH2)2), 6.82 (d, J=9.87 Hz, 2H, 3,5-C6H4—NMe2 or 2,6-C6H4—NMe2), 7.30-7.50 (m, 5H, N-Ph), 8.00 (m, 3H, 3,5-C6H4—NMe2 or 2,6-C6H4—NMe2 and imidazo[4,5-b]pyridine 5-H); 13.09 (s, 1H, imidazo[4,5-b]pyridine N—H); LC-MS (ESI, m/z) 5.10 min—504, 506 [(M+H)+, Cl isotopic pattern]; ESI-HRMS Found: 504.2278, calculated for C27H31N7ClO (M+H)+: 504.2279.

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; 1:1)

Sources & evidence

ORD record
ord-43a1aa3706a2469398c97f3d8cd65cda
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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