1,2-Dichloroethane → HCID 178520235, compound

HRID 1012056Notes

Reaction equation

HRID 1012056 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[C:20]1[C:24]([NH2:25])=[CH:23][NH:22][N:21]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CS(C)=O>[NH:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:11]=[C:12]1[C:20]1[C:24]([NH:25][C:8](=[O:10])[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:23][NH:22][N:21]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 999Phenylacetic AcidHCID 757711-HydroxybenzotriazoleHCID 178508052HCID 178508052, compound

Product 1

HCID 178520235HCID 178520235, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of phenylacetic acid (38 mg, 0.28 mmol), 3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (50 mg, 0.25 mmol), EDC (58 mg, 0.30 mmol) and HOBt (41 mg, 0.30 mmol) in DMSO (2 ml) was stirred at ambient temperature for 24 h. The reaction mixture was partitioned between EtOAc (40 ml) and water (40 ml) and the organic portion dried (MgSO4), filtered and reduced in vacuo. The residue was purified by flash column chromatography [SiO2, EtOAc-petrol (1:2, 1:1, 2:1)] to give N-[3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-2-phenyl-acetamide as a brown solid (15 mg, 19%). (LC/MS: Rt 3.26, [M+H]+ 318.13).

Workup

  1. customThe reaction mixture was partitioned between EtOAc (40 ml) and water (40 ml)
  2. dry with materialthe organic portion dried (MgSO4)
  3. filtrationfiltered
  4. customThe residue was purified by flash column chromatography [SiO2, EtOAc-petrol (1:2, 1:1, 2:1)]

Sources & evidence

ORD record
ord-f8b3779578fa4c3ba73e6c5ab26c0979
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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