Ethanol → HCID 178488881, compound

HRID 416931Notes

Reaction equation

HRID 416931 reaction equation
[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[S:23][CH:22]=[N:21][CH:20]=3)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.CCO.[CH:27](=O)[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH: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[S:23][CH:22]=[N:21][CH:20]=3)[CH2:14][CH2:13]2)=[C:4]2[N:9]=[C:27]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 24489Sodium DithioniteHCID 312444-MethoxybenzaldehydeHCID 578972065-Bromo-3-nitro-4-(4-(thiazol-5-ylmethyl)piperazin-1-yl)pyridin-2-amine

Product 1

HCID 178488881HCID 178488881, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 5-bromo-3-nitro-4-(4-(thiazol-5-ylmethyl)piperazin-1-yl)pyridin-2-amine (0.060 g, 0.15 mmol, 1 eq), EtOH (2.6 mL) and DMF (0.35 mL), p-anisaldehyde (0.022 g, 0.165 mmol, 1.1 eq) was added followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.45 mL, 0.45 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 aq NH3 until complete dissolution was observed. This solution was deposited on two preparative silica TLC plates and eluted with DCM/MeOH (v/v 94:6). The title compound was obtained after trituration with diethyl ether as a off-white solid (0.02 g, 27%); 1H-NMR (500 Mz, DMSO-d6): δ 2.61-2.69 (m, 4H, piperazine N(CH2)2), 3.61-3.67 (m, 4H, piperazine N(CH2)2), 3.84 (s, 3H, OMe), 3.86 (s, 2H, NCH2), 7.10 (d, J=9.0 Hz, 2H, ArH, C6H4), 7.82 (s, 1H, thiazole 4-H), 8.13 (d, J=9.0 Hz, 2H, ArH, C6H4), 8.20 (s, 1H, imidazo[4,5-b]pyridine 5-H), 9.05 (s, 1H, thiazole 2-H), 13.20-13.50 (br s, 1H, imidazo[4,5-b]pyridine N—H); LC (Method B)-MS (ESI, m/z): Rt=3.34 min—485/487 [(M+H+), Br isotopic pattern, 100%]. ESI-HRMS: Found: 485.0760, calculated for C21H22BrN6OS (M+H)+: 485.0759.

Workup

  1. additionwas added
  2. temperatureto cool to room temperature
  3. washeluted with DCM/MeOH (v/v 94:6)

Sources & evidence

ORD record
ord-4d0e7fcf664d4de88c2eb733f81072bf
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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