Ketoprofen → HCID 15676082, compound

HRID 974038Notes

Reaction equation

HRID 974038 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) propionoic 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 filterates were evaporated under reduced pressure to a residue, which was chlomatographed to afford 3-dimethylamino-5-(1-(3-benzoylphenyl)ethyl)-1,2,4-oxadiazole (2.00 g, 53% yield); NMR(CDCl3) δ 1.27(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 filterates were evaporated under reduced pressure to a residue, which

Sources & evidence

ORD record
ord-55af8df2368c4e36a1dd7b94eacd65d6
Source dataset
uspto-grants-1991_11
Patent number
US05066666

Reaction notes

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