Diisopropylcarbodiimide → (7-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-[4-(5-methoxy-1 H-indol-3-yl)-butyl]-amine

HRID 1290254

反応式

HRID 1290254 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][C:15](O)=O.O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.Cl.[CH3:39][O:40][C:41]1[CH:42]=[CH:43][C:44]2[O:49][CH2:48][CH:47]([CH2:50][NH2:51])[O:46][C:45]=2[CH:52]=1>CN(C=O)C>[CH3:39][O:40][C:41]1[CH:42]=[CH:43][C:44]2[O:49][CH2:48][CH:47]([CH2:50][NH:51][CH2:15][CH2:14][CH2:13][CH2:12][C:6]3[C:5]4[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=4)[NH:8][CH:7]=3)[O:46][C:45]=2[CH:52]=1

参加物

6

反応物 4

HCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 112417775-Methoxyindole-3-butyric acidHCID 189238737-Methoxy-2,3-dihydro-1,4-benzodioxin-2-methanamine hydrochloride

生成物 1

HCID 18923902(7-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-[4-(5-methoxy-1 H-indol-3-yl)-butyl]-amine収率 76.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

5-Methoxyindole-3-butyric acid (1.0 g, 4.3 mmole), 1-hydroxybenzotriazole hydrate (0.7 g, 5.2 mmole) and 1,3-diisopropylcarbodiimide (1.6 ml, 10.3 mmole) were combined in 150 ml of DMF and stirred at room temperature for 2 hours under a nitrogen atmosphere. To this was added dropwise 7-methoxy-2,3-dihydro-1,4-benzodioxin-2-methanamine hydrochloride (1.0 g, 4.3 mmole) in 50 ml of DMF and the mixture was further stirred for 24 hours. The solvent was removed and replaced with dichloromethane. The mixture was then washed with H2O. The separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was chromatographed on a silica gel column using ethyl acetate as eluant. Evaporation of product-containing fractions gave 1.3 g (74%) of the desired product, (7-methoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-4-(5-methoxy-1H-indol-3-as an off-white solid.

後処理

  1. stirringthe mixture was further stirred for 24 hours
  2. customThe solvent was removed
  3. washThe mixture was then washed with H2O
  4. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe residue was chromatographed on a silica gel column
  8. customEvaporation of product-containing fractions

出典と根拠

ORDレコード
ord-57ac7f372d1141ed8f33c4cf7fbe130c
出典データセット
uspto-grants-1998_05
特許番号
US05750724

関連ノート

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