Water → HCID 53638671, compound

HRID 457760Notes

Reaction equation

HRID 457760 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:4]=2[NH:3][CH:2]=1.Cl.C([N:16]=C=NCCCN(C)C)C.[Cl:25][C:26]1[CH:27]=[C:28]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:29]=[CH:30][C:31]=1[Cl:32].O>CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:25][C:26]1[CH:27]=[C:28]([N:33]2[CH2:38][CH2:37][N:36]([C:2]3[NH:3][C:4]4[CH:9]=[C:8]([C:10]([NH2:16])=[O:12])[CH:7]=[CH:6][C:5]=4[N:1]=3)[CH2:35][CH2:34]2)[CH:29]=[CH:30][C:31]=1[Cl:32]

Participants

7

Reactant 4

HCID 962WaterHCID 936011-(3,4-Dichlorophenyl)piperazineHCID 4594565-Benzimidazolecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 53638671HCID 53638671, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Benzimidazole-5-carboxylic acid (1 mMol, 162 mg) was dissolved in 5 mL dry DMF and reacted with 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride for 15 minutes. 1-(3,4-dichlorophenyl)-piperazine, 1 mMol (231 mg) was added followed by 10 mg DMAP. The mixture was stirred for 20 h at room temperature. The reaction mixture was poured into water and extracted with methylene chloride (3×50 mL). The extracts were combined, washed with brine, water and dried over MgSO4. After evaporation of the solvent, the residue was chromatographed on silica gel with chloroform-methanol (0–5% methanol, gradient). Evaporation of the desired fractions gave 150 mg (40%) of the title compound; MS (ESI) m/e 375 (M+).

Workup

  1. extractionextracted with methylene chloride (3×50 mL)
  2. washwashed with brine, water
  3. dry with materialdried over MgSO4
  4. customAfter evaporation of the solvent
  5. customthe residue was chromatographed on silica gel with chloroform-methanol (0–5% methanol, gradient)
  6. customEvaporation of the desired fractions

Sources & evidence

ORD record
ord-b11a2ec25ec64730aaf7ad8caef4b36f
Source dataset
uspto-grants-2007_03
Patent number
US07189739B2

Reaction notes

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