Ethanol → HCID 178432928, compound

HRID 416912Notes

Reaction equation

HRID 416912 reaction equation
[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[N:20]=[C:21]([CH3:24])[S:22][CH:23]=3)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.CCO.[N:28]1([C:34]2[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(Cl)Cl.N.CN(C=O)C>[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[N:20]=[C:21]([CH3:24])[S:22][CH:23]=3)[CH2:14][CH2:13]2)=[C:4]2[N:9]=[C:38]([C:37]3[CH:36]=[CH:35][C:34]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:41][CH:40]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 24489Sodium DithioniteHCID 2913494-MorpholinobenzaldehydeHCID 578971595-Bromo-4-(4-((2-methylthiazol-4-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine

Product 1

HCID 178432928HCID 178432928, compoundYield 30.7%

Reagents, catalysts & solvents 3

HCID 222AmmoniaCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 5-bromo-4-(4-((2-methylthiazol-4-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine (0.041 g, 0.10 mmol), EtOH (2.6 mL) and DMF (0.35 mL), 4-morpholin-4-yl-benzaldehyde (0.021 g, 0.11 mmol) was added followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.30 mL, 0.3 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 solid (0.017 g, 30%); 1H-NMR (500 Mz, DMSO-d6): δ 2.63-2.70 (m, 7H), 3.21-3.27 (m, 4H), 3.60-3.68 (m, 6H), 3.76 (m, 4H), 7.07 (d, J=9.0 Hz, 2H, ArH, C6H4), 7.31 (s, 1H, thiazole 5-H), 8.05 (d, J=8.0 Hz, 2H, ArH, C6H4), 8.17 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.22 (br s, 1H, imidazo[4,5-b]pyridine N—H); LC (Method B)-MS (ESI, m/z) 3.29 min—554/556 [(M+H)+, Br isotopic pattern]. ESI-HRMS: Found: 554.1345, calculated for C25H29BrN7OS (M+H)+: 554.1338.

Workup

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

Sources & evidence

ORD record
ord-77a6630adbd94a7ca3698f1c8362327b
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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