1,2-Dichloroethane → N-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-3,4-dihydroxy-5-methoxybenzamide
Reaction equation
Cl.[CH3:2][C:3]1[C:7]([CH2:8][N:9]2[CH:13]=[C:12]([NH2:14])[CH:11]=[N:10]2)=[C:6]([CH3:15])[O:5][N:4]=1.[OH:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([O:27][CH3:28])[C:25]=1[OH:26])[C:20](O)=[O:21].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C>[CH3:2][C:3]1[C:7]([CH2:8][N:9]2[CH:13]=[C:12]([NH:14][C:20](=[O:21])[C:19]3[CH:23]=[C:24]([O:27][CH3:28])[C:25]([OH:26])=[C:17]([OH:16])[CH:18]=3)[CH:11]=[N:10]2)=[C:6]([CH3:15])[O:5][N:4]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-amine hydrochloride (example 4-1a) (228 mg, 1 mmol), 3,4-dihydroxy-5-methoxybenzoic acid (184 mg, 1 mmol), HOBt (135 mg, 1 mmol), and EDC (191 mg, 1 mmol) were dissolved in 2 mL DMF in a microwave vial followed by the addition of triethylamine (101 mg, 1 mmol). The reaction was placed in a microwave reactor at 165° C. for 5 minutes. The crude product was purified directly using Varian HPLC (10%-95% ACN in H2O: 25 minute gradient). The pure fractions were combined and concentrated to afford N-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-3,4-dihydroxy-5-methoxybenzamide. (280 mg, 70%). LC/MS; [M+H] calculated for C17H18N4O5; expected 359.1; found 359.1.
Workup
- customThe crude product was purified directly
- customHPLC (10%-95% ACN in H2O: 25 minute gradient)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d3930e733f7f4522a36fd63a3cef07fc
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08076491B2
Reaction notes
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