4-(Dimethylamino)Benzaldehyde → HCID 178482671, compound

HRID 416939Notes

Reaction equation

HRID 416939 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:26][N:27]([CH3:36])[C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>CCO.CN(C=O)C.C(Cl)Cl.N>[Cl:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:14][CH2:13]2)=[C:4]2[N:9]=[C:32]([C:31]3[CH:34]=[CH:35][C:28]([N:27]([CH3:36])[CH3:26])=[CH:29][CH:30]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 3

HCID 74794-(Dimethylamino)BenzaldehydeHCID 24489Sodium DithioniteHCID 57897205HCID 57897205, compound

Product 1

HCID 178482671HCID 178482671, compoundYield 16%

Reagents, catalysts & solvents 4

HCID 222AmmoniaCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 5-chloro-3-nitro-4-(4-phenethylpiperazin-1-yl)pyridin-2-amine (0.058 g, 0.16 mmol) in EtOH (2.8 mL) and DMF (0.37 mL), 4-(dimethylamino)benzaldehyde (0.026 g, 0.18 mmol, 1.1 eq) was added followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.48 mL, 0.48 mmol). The reaction mixture was heated at 85° C. for 24 h, then allowed to cool to room temperature and diluted with DCM and a few drops of aqueous NH3 until complete dissolution was observed. This solution was deposited on two preparative silica TLC plates and eluted with DCM/MeOH (v/v; 99:1) to give the title compound as a solid (0.0012 g, 16%); 1H-NMR (500 Mz, DMSO-d6): δ 2.57-2.64 (m, 2H), 2.64-2.70 (m, 4H, piperazine N(CH2)2), 2.77-2.83 (m, 2H), 3.00 (s, 6H, NMe2), 3.65-3.70 (m, 4H piperazine N(CH2)2), 6.82 (d, J=9.0 Hz, 2H, ArH), 7.16-7.22 (m, 1H, ArH, C6H5), 7.25-7.32 (m, 4H, ArH), 7.98-8.04 (m, 3H, imidazo[4,5-b]pyridine 5-H and ArH), 13.09 (br s, 1H, imidazo[4,5-b]pyridine N—H); LC (Method B)-MS (ESI, m/z): Rt=3.59 min—461/463 [(M+H)+, Cl isotopic pattern]. ESI-HRMS: Found: 461.2214, calculated for C26H30ClN6 (M+H)+: 461.2220;

Workup

  1. additionwas added
  2. temperatureto cool to room temperature
  3. washeluted with DCM/MeOH (v/v; 99:1)

Sources & evidence

ORD record
ord-19355fd8c29049d28b25be87009bb792
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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