1,2-Dichloroethane → cyclohexanecarboxylic acid [3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-amide

HRID 1012055Notes

Reaction equation

HRID 1012055 reaction equation
[CH:1]1([C:7]([OH:9])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[C:19]1[C:23]([NH2:24])=[CH:22][NH:21][N:20]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CS(C)=O>[NH:12]1[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:10]=[C:11]1[C:19]1[C:23]([NH:24][C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[O:9])=[CH:22][NH:21][N:20]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7413Cyclohexanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 178508052HCID 178508052, compound

Product 1

HCID 178522418cyclohexanecarboxylic acid [3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-amideYield 32.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of cyclohexanecarboxylic acid (36 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 (1:4, 1:3, 1:2, 1:1)] affording cyclohexanecarboxylic acid [3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-amide as an off-white solid (25 mg, 32%). (LC/MS: Rt 3.59, [M+H]+ 310.16).

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 (1:4, 1:3, 1:2, 1:1)]

Sources & evidence

ORD record
ord-0080935165ce4572b099b98f55830e10
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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