Aspirin → HCID 22372654, compound

HRID 1379169Notes

Reaction equation

HRID 1379169 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:27])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][NH2:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[C:28]([O:31][C:32]1[C:33](=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:34](O)=[O:35])(=[O:30])[CH3:29].ON1C2C=CC=CC=2N=N1>C(#N)C.CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:27])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][NH:24][C:34](=[O:35])[C:33]3[CH:37]=[CH:38][CH:39]=[CH:40][C:32]=3[O:31][C:28](=[O:30])[CH3:29])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 2244AspirinHCID 757711-HydroxybenzotriazoleHCID 177287Davasaicin

Product 1

HCID 22372654HCID 22372654, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

0.27 g (0.66 mmol) of N-{3-(3,4-dimethylphenyl)propyl}-4-(2-aminoethoxy)-3-methoxyphenylacetamide obtained in Step 5 of Example 3, 0.17 g (0.94 mmol) of acetylsalicylic acid and 0.10 g (0.74 mmol) of 1-hydroxylbenzotriazole were dissolved in 15 ml of a mixture of acetonitrile and dimethylformamide(1:2). 0.19 g (0.92 mmol) of dicyclohexanecarbodiimide was added thereto and the resultant mixture was stirred at a room temperature for 2 days. White precipitates were removed and the remaining solution was diluted with 30 ml of dichloromethane, which was washed with water and dried. After removing the solvent under a reduced pressure, the residue was subjected to silica gel chromatography to obtain 0.22 g of the title compound (yield: 63%).

Workup

  1. addition0.19 g (0.92 mmol) of dicyclohexanecarbodiimide was added
  2. customWhite precipitates
  3. customwere removed
  4. additionthe remaining solution was diluted with 30 ml of dichloromethane, which
  5. washwas washed with water
  6. customdried
  7. customAfter removing the solvent under a reduced pressure

Sources & evidence

ORD record
ord-684ffb7c00ee4ed18c0f54daf0910b67
Source dataset
uspto-grants-1997_09
Patent number
US05670546

Reaction notes

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