Ethanol → HCID 178488884, compound

HRID 416886Notes

Reaction equation

HRID 416886 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.C(O)C.[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>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:34]([C:33]3[CH:36]=[CH:37][C:30]([O:29][CH3:28])=[CH:31][CH:32]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 24489Sodium DithioniteHCID 312444-MethoxybenzaldehydeHCID 578971595-Bromo-4-(4-((2-methylthiazol-4-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine

Product 1

HCID 178488884HCID 178488884, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 (0.062 g, 0.15 mmol), ethanol (0.85 mL), DMF (0.15 mL) and 4-methoxybenzaldehyde (0.022 g, 0.165 mmol) was added a freshly prepared aqueous solution of Na2S2O4 (1M; 0.45 mL, 0.45 mmol). The reaction mixture was heated at 85° C. for 17 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on preparative silica TLC plates, which were eluted with dichloromethane/methanol (v/v; 9:1). The isolated compound was further purified by column chromatography on a Biotage SP1 system eluting with methanol (2-10%) in dichloromethane. The title compound was obtained as a yellow solid after trituration with diethyl ether (0.010 g, 13%); 1H-NMR (500 Mz, DMSO-d6): δ 2.62-2.73 (m, 4H, piperazine N(CH2)2), 3.18 (s, 3H, Me), 3.60-3.74 (m, 4H, piperazine N(CH2)2), 3.85 (s, 3H, OMe), 4.00-4.20 (br s, 2H, NCH2), 7.11 (d, J=8.5 Hz, 2H, ArH), 7.33 (s, 1H, thiazole 5-H), 8.15 (d, J=9.0 Hz, 2H, ArH), 8.21 (s, 1H, imidazo[4,5-b]pyridine 5-H); LC (Method B)-MS (ESI, m/z) 3.14 min—499/501 [(M+H)+, Br isotopic pattern]. ESI-HRMS: Found: 499.0916, calculated for C22H23BrN6OS (M+H)+: 499.0915.

Workup

  1. temperatureto cool to room temperature
  2. customthe solvents were removed in vacuo
  3. customThe residue was absorbed on preparative silica TLC plates, which
  4. washwere eluted with dichloromethane/methanol (v/v; 9:1)
  5. customThe isolated compound was further purified by column chromatography on a Biotage SP1 system
  6. washeluting with methanol (2-10%) in dichloromethane

Sources & evidence

ORD record
ord-a117e43921874d9d94ed70a2db86a9d5
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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