HCID 59869005, compound → HCID 59160539, compound

HRID 1958672Notes

Reaction equation

HRID 1958672 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=3)=[N:10][C:9]=2[C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[N:29]=[CH:28][CH:27]=[CH:26]3)[CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N:20]4[CH2:4][CH2:3][CH2:2][CH2:1]4)[CH:15]=3)=[N:10][C:9]=2[C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[N:29]=[CH:28][CH:27]=[CH:26]3)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 59869005HCID 59869005, compound

Product 1

HCID 59160539HCID 59160539, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-(5-(6-methylpyridin-2-yl)-2-(3-nitrobenzyl)-1H-imidazol-4-yl)quinoline (500 mg, 1.186 mmol, prepared according to the method described in US 2008/0319012 A1) in MeOH (5 mL) was added Pd/C (0.5 mg, 10% w/w) and the mixture was stirred under H2 at atmospheric pressure for 5 hours. The reaction mixture was filtered through celite and the filterate was concentrated under reduced pressure. The residue was purified by MPLC on silica gel (MeOH:CH2Cl2=1:50) to afford the 3-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)aniline (424 mg, 91%). The obtained compound, 3-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)aniline (30 mg, 0.077 mmol) was dissolved in DMF (3 mL), treated with 1,4-dibromobutane (17 mg, 0.080 mmol), and stirred at 120° C. for 12 hours. The reaction mixture was cooled to room temperature, added H2O (30 mL), and extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by MPLC (MeOH:CH2Cl2=1:20 (v/v)) and on NH silica gel (MeOH:CH2Cl2=1:100 (v/v)) to afford the title compound (7 mg, 20.5%). (300 MHz, CDCl3) δ 2.50 (3H, s), 4.09 (2H, s), 6.64-6.72 (2H, m), 6.91-6.98 (2H, m), 7.31 (1H, d), 7.39 (1H, t), 8.13 (2H, d), 8.41 (1H, s), 8.84 (2H, dd), MS (ESI) m/z 411 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filterate was concentrated under reduced pressure
  3. customThe residue was purified by MPLC on silica gel (MeOH:CH2Cl2=1:50)

Sources & evidence

ORD record
ord-23dfae97c10b4f3e9664ebdb7e1894f7
Source dataset
uspto-grants-2013_04
Patent number
US08410146B2

Reaction notes

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