Naphthalic anhydride → [3-[[3-(1,3-dioxo-3a,9b-dihydro-1H,3H-benzo[de]isoquinolin-2-yl)propyl]methylamino]propyl]carbamic acid tert-butyl ester

HRID 12258

反応式

HRID 12258 の反応式
[CH:1]1[CH:2]=[C:3]2[C:8]3=[C:9]([C:11]([O:13][C:14](=[O:15])[C:7]3=[CH:6][CH:5]=[CH:4]2)=O)[CH:10]=1.[C:16]([O:20][C:21](=[O:32])[NH:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH2:29][CH2:30][NH2:31])[CH3:27])([CH3:19])([CH3:18])[CH3:17]>C(O)C>[C:16]([O:20][C:21](=[O:32])[NH:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH2:29][CH2:30][N:31]1[C:11](=[O:13])[CH:9]2[CH:10]=[CH:1][CH:2]=[C:3]3[CH:8]2[C:7](=[CH:6][CH:5]=[CH:4]3)[C:14]1=[O:15])[CH3:27])([CH3:19])([CH3:17])[CH3:18]

参加物

4

反応物 2

HCID 6693Naphthalic anhydrideHCID 12983660tert-butyl N-{3-[(3-aminopropyl)(methyl)amino]propyl}carbamate

生成物 1

HCID 86612376[3-[[3-(1,3-dioxo-3a,9b-dihydro-1H,3H-benzo[de]isoquinolin-2-yl)propyl]methylamino]propyl]carbamic acid tert-butyl ester収率 90%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

1,8-naphthalic anhydride (0.18 g, 0.9 mmol) was added to a solution of [3-[(3-aminopropyl)methylamino]propyl]carbamic acid tert-butyl ester previously prepared (Spicer at el., Bioorg. Med. Chem. 2002, vol. 10, p. 19) (0.2 g, 0.8 mmol) in absolute ethanol (20 ml). The reaction mixture was heated at reflux overnight. Removal of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 50:1) yielded [3-[[3-(1,3-dioxo-3a,9b-dihydro-1H,3H-benzo[de]isoquinolin-2-yl)propyl]methylamino]propyl]carbamic acid tert-butyl ester (0.37 g, 90%) as a foam.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customRemoval of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 50:1)

出典と根拠

ORDレコード
ord-2a5afcdb095849ddb861073e42e5abbe
出典データセット
uspto-grants-2010_06
特許番号
US07728000B2

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