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

HRID 431583노트

반응식

HRID 431583 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

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. MS: m/e=357.3. (M+H+).

후처리

  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)

출처 및 근거

ORD 기록
ord-e5b16f949dd1472b978f7b23ede30004
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660736B2

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