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

HRID 1070685ノート

反応式

HRID 1070685 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-98978208981f4f318f9183e5128c7a7b
出典データセット
uspto-grants-2005_06
特許番号
US06903095B2

反応ノート

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