1,2-Dichloroethane → HCID 178490812, compound

HRID 1012135Notes

Reaction equation

HRID 1012135 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([NH2:15])[C:11]([NH2:14])=[CH:12][CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:16][O:17][C:18]1[CH:35]=[CH:34][C:21]([CH2:22][N:23]2[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[C:25]([C:31](O)=O)=[N:24]2)=[CH:20][CH:19]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][N:23]2[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[C:25]([C:31]3[NH:14][C:11]4[CH:12]=[CH:13][C:8]([CH2:7][N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)=[CH:9][C:10]=4[N:15]=3)=[N:24]2)=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 251933094-(Morpholinomethyl)benzene-1,2-diamineHCID 671060171-[(4-Methoxyphenyl)methyl]-4-nitro-1H-pyrazole-3-carboxylic acid

Product 1

HCID 178490812HCID 178490812, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-morpholin-4-ylmethyl-benzene-1,2-diamine (2.5 g, 12 mmol), 1-(4-methoxy-benzyl)-4-nitro-1H-pyrazole-3-carboxylic acid (2.91 g, 10 mmol), EDC (2.3 g, 12 mmol) and HOBt (1.62 g, 12 mmol) in dry DMF (40 ml) was stirred at ambient temperature for 24 h. The mixture was reduced in vacuo, the residue partitioned between EtOAc (100 ml) and water (50 ml) and the organic portion washed with saturated aqueous sodium hydrogen carbonate, dried (MgSO4) and reduced in vacuo. The residue was dissolved in AcOH (70 ml) and heated at reflux for 3 h. The solvent was removed in vacuo and the residue purified by flash column chromatography [SiO2, MeOH:DCM (5:95)] to give 2-[1-(4-methoxy-benzyl)-4-nitro-1H-pyrazol-3-yl]-5-morpholin-4-ylmethyl-1H-benzimidazole (2 g, 37%) as a yellow foam. (LC/MS: Rt 1.91, [M+H]+ 449).

Workup

  1. customthe residue partitioned between EtOAc (100 ml) and water (50 ml)
  2. washthe organic portion washed with saturated aqueous sodium hydrogen carbonate
  3. dry with materialdried (MgSO4)
  4. dissolutionThe residue was dissolved in AcOH (70 ml)
  5. temperatureheated
  6. temperatureat reflux for 3 h
  7. customThe solvent was removed in vacuo
  8. customthe residue purified by flash column chromatography [SiO2, MeOH:DCM (5:95)]

Sources & evidence

ORD record
ord-71e054203e78461b837a2479960fe9c3
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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