1-[(1-Methyl-1H-imidazol-2-yl)methyl]piperazine → HCID 46866894, compound

HRID 416922Notes

Reaction equation

HRID 416922 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[Br:14][C:15]1[C:16](Cl)=[C:17]([N+:22]([O-:24])=[O:23])[C:18]([NH2:21])=[N:19][CH:20]=1>CC(O)C.CCN(C(C)C)C(C)C>[Br:14][C:15]1[C:16]([N:11]2[CH2:10][CH2:9][N:8]([CH2:7][C:3]3[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=3)[CH2:13][CH2:12]2)=[C:17]([N+:22]([O-:24])=[O:23])[C:18]([NH2:21])=[N:19][CH:20]=1

Participants

5

Reactant 2

HCID 431120931-[(1-Methyl-1H-imidazol-2-yl)methyl]piperazineHCID 454802365-Bromo-4-chloro-3-nitropyridin-2-amine

Product 1

HCID 46866894HCID 46866894, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
65 °C

Procedure

The resulting 1-((1-methyl-1H-imidazol-2-yl)methyl)piperazine (supposedly 0.320 g, 1.78 mmol, 1 eq) was suspended in iPrOH (5.4 mL) and DIPEA (1.4 mL). To this solution, 5-bromo-4-chloro-3-nitropyridin-2-amine (0.400 g, 1.62 mmol, 1 eq) was added and the mixture heated and stirred for 17 h at 65° C. The mixture was filtered, washed with iPrOH (3×6 mL), Et2O (2×6 mL) and dried to give the title compound as a bright yellow powder (0.370 g, 51%); 1H-NMR (500 MHz, DMSO-d6): δ 2.97-3.08 (br s, 4H, piperazine N(CH2)2), 3.57 (s, 2H, NCH2), 3.66 (s, 3H, imidazole Me), 6.75 (s, 1H, imidazole H-4), 6.96 (s, 2H, NH2), 7.08 (s, 1H, imidazole H-5), 8.16 (s, 1H, pyridine 6-H); LC (Method B)-MS (ESI, m/z): Rt=2.07 min—396/398 [(M+H+), Br isotopic pattern, 100%].

Workup

  1. temperaturethe mixture heated
  2. filtrationThe mixture was filtered
  3. washwashed with iPrOH (3×6 mL), Et2O (2×6 mL)
  4. customdried

Sources & evidence

ORD record
ord-7ca818ab3bdd4026ba81ad2a20395729
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

Loading…