Ketoprofen → HCID 15676082, compound

HRID 1646561Notes

Reaction equation

HRID 1646561 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:15]([CH3:19])[C:16](O)=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN[N:23](NC)[C:24](N)=[N:25]O.O[N:31]1[C:35]2C=CC=CC=2N=N1.[CH:40]1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C>CN(C)C=O>[CH3:40][N:31]([CH3:35])[C:24]1[N:25]=[C:16]([CH:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)[CH3:19])[O:17][N:23]=1

Participants

7

Reactant 5

HCID 3825KetoprofenHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 86743838HCID 86743838, compound

Product 1

HCID 15676082HCID 15676082, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the mixture of 2-(3-benzoylphenyl) propionic acid (3.00 g, 11.8 mmol), 1,1-dimethylamino-2-hydroxyguanidine hydrochloride (1.98 g, 14.2 mmol), N-hydroxybenztriazole (1.91 g, 14.2 mmol) and dicyclohexylcarbodiimide (2.92 g, 14.2 mmol) in N,N-dimethylformamide (100 ml) were added triethylamine (1.43 g, 14.2 mmol). After the addition, the mixture was stirred at room temperature for 12 hr, then filterated. The filtrates were evaporated under reduced pressure to a residue, which wash chlomatographed to afford 3-dimethylamino-5-(1-(3-benzoylphenyl)ethyl)-1,2,4-oxadiazole (2.00 g, 53% yield); NMR(CDCl3)δ1.27(d, 3H), 3.00(s, 6H), 4.32(q, 1H), 7.30-7.99(m, 9H) ppm; IR(neat) 1660, 1595, 1400, 1280 cm-1.

Workup

  1. additionAfter the addition
  2. customThe filtrates were evaporated under reduced pressure to a residue, which
  3. washwash

Sources & evidence

ORD record
ord-11f28340e7b3465eb6424f0fb4332be2
Source dataset
uspto-grants-1993_01
Patent number
US05180731

Reaction notes

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