4-Iodo-2-methoxynicotinaldehyde → 1-{4-[2-(4-Iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzimidazol-5-yl]-piperazin-1-yl}-ethanone

HRID 1354615Notes

Reaction equation

HRID 1354615 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:18])[CH3:17])[CH2:12][CH2:11]2)[CH:5]=[C:6]([CH3:9])[C:7]=1[NH2:8].[I:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([O:26][CH3:27])[C:21]=1[CH:28]=O>CO>[I:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([O:26][CH3:27])[C:21]=1[C:28]1[NH:1][C:2]2[CH:3]=[C:4]([N:10]3[CH2:11][CH2:12][N:13]([C:16](=[O:18])[CH3:17])[CH2:14][CH2:15]3)[CH:5]=[C:6]([CH3:9])[C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 100383814-Iodo-2-methoxynicotinaldehydeHCID 220210411-[4-(3,4-Diamino-5-methyl-phenyl)-piperazin-1-yl]-ethanone

Product 1

HCID 220213071-{4-[2-(4-Iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzimidazol-5-yl]-piperazin-1-yl}-ethanoneYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[4-(3,4-diamino-5-methyl-phenyl)-piperazin-1-yl]-ethanone (4.00 g, 16.18 mmol) in methanol (100 mL) was added 4-iodo-2-methoxy-pyridine-3-carbaldehyde (4.25 g, 16.18 mmol). The reaction mixture was stirred at room temperature for 14 h. After concentration, the residue was purified by flash column chromatography (10% MeOH/CH2Cl2) to yield the title compound (5.25 g, 66%). 1H NMR (400 MHz, CD3OD) δ 7.81 (1H, d, J=5.4 Hz), 7.48 (1H, d, J=5.4 Hz), 7.26 (1H, s), 6.85 (1H, s), 3.85 (3H, s), 3.78 (2H, t, J=5.0 Hz), 3.64 (2H, t, J=5.0 Hz), 3.16 (2H, t, J=5.2 Hz), 3.11 (2H, t, J=5.2 Hz), 2.62 (3H, s), 2.13 (3H, s). LCMS (M+H)+ m/z 492 (t=1.71 min.).

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by flash column chromatography (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-8fa362101b0a451d8b0ca5fd88ef0b17
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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