2,4-Dichloroquinoline-3-carbaldehyde → 1-{4-[2-(2,4-Dichloro-quinoline-3yl)-7-methyl-3H-benzimidazole-5-yl]-piperazin-1-yl}-ethanone

HRID 1767022Notes

Reaction equation

HRID 1767022 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].[Cl:19][C:20]1[C:29]([CH:30]=O)=[C:28]([Cl:32])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1>CO>[Cl:19][C:20]1[C:29]([C:30]2[NH:1][C:2]3[CH:3]=[C:4]([N:10]4[CH2:11][CH2:12][N:13]([C:16](=[O:18])[CH3:17])[CH2:14][CH2:15]4)[CH:5]=[C:6]([CH3:9])[C:7]=3[N:8]=2)=[C:28]([Cl:32])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1

Participants

4

Reactant 2

HCID 149205162,4-Dichloroquinoline-3-carbaldehydeHCID 220210411-[4-(3,4-Diamino-5-methyl-phenyl)-piperazin-1-yl]-ethanone

Product 1

HCID 211131281-{4-[2-(2,4-Dichloro-quinoline-3yl)-7-methyl-3H-benzimidazole-5-yl]-piperazin-1-yl}-ethanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3.6 mmol of 1-[4-(3,4-Diamino-5-methyl-phenyl)-piperazin-1-yl]-ethanone was taken in 40 mL of methanol, to which was added 0.921 gm (3.6 mmol) of the 2,4-Dichloro-quinoline-3-carboxaldehyde, and the mixture was stirred for 10 hrs at room temperature, solvent was evaporated to dryness, and the residue was chromatographed to provide the product. LRMS [M+H]+454; 1H NMR (400 MHz, CDCl3) δ 8.12 (d, 1H, J=7.6 Hz), 8.04 (d, 1H, J=8.4 Hz), 7.85 (dd, 1H, J=7.6, 8.4 Hz), 7.78 (dd, 1H, J=7.6, 8.4 Hz), 6.86 (brs, 1H), 6.83(brs, 1H), 3.76 (br, 2H), 3.62 (br, 2H), 3.15 (br, 2H), 3.01 (br, 2H), 2.66 (s, 3H), 2.22 (s, 3H).

Workup

  1. customsolvent was evaporated to dryness
  2. customthe residue was chromatographed
  3. customto provide the product

Sources & evidence

ORD record
ord-222f1b9120e943fcb8eca3408c63dc9d
Source dataset
uspto-grants-2007_06
Patent number
US07232826B2

Reaction notes

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