1,2-Dichloroethane → 5-methyl-3-phenyl-isoxazole-4-carboxylic acid [3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-amide

HRID 1012057Notes

Reaction equation

HRID 1012057 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([OH:15])=O.[NH:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[C:25]1[C:29]([NH2:30])=[CH:28][NH:27][N:26]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CS(C)=O>[NH:18]1[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:16]=[C:17]1[C:25]1[C:29]([NH:30][C:13]([C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[O:15])=[CH:28][NH:27][N:26]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 143435-Methyl-3-phenylisoxazole-4-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 178508052HCID 178508052, compound

Product 1

HCID 1784349845-methyl-3-phenyl-isoxazole-4-carboxylic acid [3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-amideYield 16%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5-methyl-3-phenylisoxazole-4-carboxylic acid (57 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 and water 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)] affording 5-methyl-3-phenyl-isoxazole-4-carboxylic acid [3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-amide as a cream solid (15 mg, 16%). (LC/MS: Rt 3.73, [M+H]+ 385.14).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  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-2c8351ec39ad482ca5bcfc66573b1b3d
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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