1,2-Dichloroethane → N-[3-(2H-Benzimidazol-2-ylidene)-2,3-dihydro-1H-pyrazol-4-yl]-3-methoxybenzamide

HRID 1012083Notes

Reaction equation

HRID 1012083 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[C:21]1[C:25]([NH2:26])=[CH:24][NH:23][N:22]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CS(C)=O.O>[NH:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:12]=[C:13]1[C:21]1[C:25]([NH:26][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:24][NH:23][N:22]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 114613-Methoxybenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 178508052HCID 178508052, compound

Product 1

HCID 178490490N-[3-(2H-Benzimidazol-2-ylidene)-2,3-dihydro-1H-pyrazol-4-yl]-3-methoxybenzamideYield 13%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 3-methoxybenzoic acid (84 mg, 0.55 mmol), 3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (100 mg, 0.50 mmol), EDC (116 mg, 0.60 mmol) and HOBt (81 mg, 0.60 mmol) was stirred at ambient temperature in DMSO (3 ml) for 20 h. The reaction mixture was poured into water (30 ml) and the resultant solid was collected by filtration and purified by flash column chromatography [SiO2, (dichloromethane 120 ml, methanol 15, acetic acid 3 ml, water 2 ml (DMAW 120)] to yield N-[3-(1H-Benzimidazol-2-yl)-1H-pyrazol-4-yl]-3-methoxy-benzamide as a pale pink-gray solid (21 mg, 13%). (LC/MS: Rt 3.81, [M+H]+ 334.03).

Workup

  1. filtrationthe resultant solid was collected by filtration
  2. custompurified by flash column chromatography [SiO2

Sources & evidence

ORD record
ord-0db6d0ba4466492dbd890bdfb0092f19
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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