Sodium Dithionite → HCID 178488887, compound

HRID 416900Notes

Reaction equation

HRID 416900 reaction equation
[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[S:20][CH:21]=[CH:22][N:23]=3)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH:24](=O)[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>CCO.C(Cl)Cl.N>[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[S:20][CH:21]=[CH:22][N:23]=3)[CH2:14][CH2:13]2)=[C:4]2[N:9]=[C:24]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 24489Sodium DithioniteHCID 312444-MethoxybenzaldehydeHCID 57897270HCID 57897270, compound

Product 1

HCID 178488887HCID 178488887, compoundYield 25.2%

Reagents, catalysts & solvents 3

HCID 222AmmoniaCatalystHCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 5-bromo-3-nitro-4-(4-(thiazol-2-ylmethyl)piperazin-1-yl)pyridin-2-amine (0.072 g, 0.18 mmol) and EtOH (2 mL), p-anisaldehyde (0.079 g, 0.20 mmol) in EtOH (2 mL) was added followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.54 mL, 0.54 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; 96:4) to give the title compound as a off-white solid (0.022 g, 25%); 1H-NMR (500 Mz, DMSO-d6): δ 2.75 (m, 4H, piperazine N(CH2)2), 3.65-3.73 (m, 4H, piperazine N(CH2)2), 3.84 (s, 3H, OMe), 3.95 (s, 2H, NCH2), 7.11 (d, J=9.0 Hz, 2H, ArH, C6H4—OMe), 7.69 (d, J=3.5 Hz, 1H, thiazole 5-H), 7.75 (d, J=3.0 Hz, 1H, thiazole 4-H), 8.14 (d, J=9.0 Hz, 2H, ArH, C6H4—OMe), 8.21 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.36 (br s, 1H, imidazo[4,5-b]pyridine N—H); LC (Method B)-MS (ESI, m/z) 4.10 min—485/487 [(M+H)+, Br isotopic pattern]. ESI-HRMS: Found: 485.0759, calculated for C21H22BrN6OS (M+H)+: 485.0748.

Workup

  1. additionwas added
  2. temperatureto cool to room temperature
  3. washeluted with DCM/MeOH (v/v; 96:4)

Sources & evidence

ORD record
ord-1a9a36c5efd449cb96ea4130bc2795ed
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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