N-(2-aminoethyl)acetamide → N-{2-[5-(4-Fluoro-benzyloxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-ethyl}-acetamide

HRID 1070685Notes

Reaction equation

HRID 1070685 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]([C:17]([OH:19])=O)[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=O)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:34]([NH:37][CH2:38][CH2:39][NH2:40])(=[O:36])[CH3:35]>CN(C)C(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]3[C:11](=[CH:15][CH:16]=2)[C:12](=[O:14])[N:40]([CH2:39][CH2:38][NH:37][C:34](=[O:36])[CH3:35])[C:17]3=[O:19])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 66082N-(2-aminoethyl)acetamideHCID 682631,1'-CarbonyldiimidazoleHCID 223970954-(4-Fluoro-benzyloxy)-phthalic acid

Product 1

HCID 22397094N-{2-[5-(4-Fluoro-benzyloxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-ethyl}-acetamideYield 62%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 4-(4-fluoro-benzyloxy)-phthalic acid (185 mg, 0.64 mmol) and carbonyldiimidazole (109 mg, 0.67 mmol) in N,N-dimethylacetamide (3 mL) was stirred at room temperature for 10 min and then heated at 50° C. for 15 min. To this mixture was added N-acetylethylenediamine (78 mg, 0.76 mmol) and the resulting mixture heated under reflux for 20 min. After cooling to room temperature, the mixture was evaporated and the residue was purified by chromatography (SiO2, CH2Cl2: 2N NH3/MeOH 98:2 to 9:1) to afford the title compound (139 mg, 62%) as an off-white solid.

Workup

  1. temperatureheated at 50° C. for 15 min
  2. temperaturethe resulting mixture heated
  3. temperatureunder reflux for 20 min
  4. temperatureAfter cooling to room temperature
  5. customthe mixture was evaporated
  6. customthe residue was purified by chromatography (SiO2, CH2Cl2: 2N NH3/MeOH 98:2 to 9:1)

Sources & evidence

ORD record
ord-98978208981f4f318f9183e5128c7a7b
Source dataset
uspto-grants-2005_06
Patent number
US06903095B2

Reaction notes

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