p-Anisoyl chloride → HCID 11248427, compound

HRID 1986357Notes

Reaction equation

HRID 1986357 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:8][C:9]2[N:14]=[CH:13][C:12]3[N:15]=[C:16]([C:20]4[C:21]([NH2:25])=[N:22][O:23][N:24]=4)[N:17]([CH2:18][CH3:19])[C:11]=3[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:33][O:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1>CN(C=O)C.O.CCOC(C)=O>[NH2:25][C:21]1[C:20]([C:16]2[N:17]([CH2:18][CH3:19])[C:11]3[CH:10]=[C:9]([O:8][C:4]4[CH:3]=[C:2]([NH:1][C:39](=[O:40])[C:38]5[CH:42]=[CH:43][C:35]([O:34][CH3:33])=[CH:36][CH:37]=5)[CH:7]=[CH:6][CH:5]=4)[N:14]=[CH:13][C:12]=3[N:15]=2)=[N:24][O:23][N:22]=1

Participants

7

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 11404963HCID 11404963, compound

Product 1

HCID 11248427HCID 11248427, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of 0.10 g of the product of Example 3 (0.30 mmols) in DMF (1.0 mL) was added 0.041 mL of triethylamine (0.30 mmols) and 0.056 g of 4-methoxybenzoylchloride (0.33 mmols). The reaction mixture was allowed to warm to rt and stirred for 23 h. The reaction mixture was diluted with 1 mL of water and 5 mL of EtOAc. The layers were separated, and the aqueous layer was extracted with EtOAc. The combined organics were washed with water and concentrated to a partial volume. Methanol was added, and a solid precipitated from the solution. The precipitate was filtered off and dried and the crude product was purified by silica gel chromatography to provide the title compound as a white powder (0.029 g, 21%). MS (ES+) m/e 473 [M+H]+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organics were washed with water
  4. concentrationconcentrated to a partial volume
  5. additionMethanol was added
  6. customa solid precipitated from the solution
  7. filtrationThe precipitate was filtered off
  8. customdried
  9. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0f7457204ff94902ac87865048294006
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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