Indole-3-Butyric Acid → [4-(1H-Indol-3-yl)-butyl]-(7-methoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)amine

HRID 1290249

反応式

HRID 1290249 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][C:13](O)=O)=[CH:2]1.O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.Cl.[CH3:37][O:38][C:39]1[CH:40]=[CH:41][C:42]2[O:47][CH2:46][C@H:45]([CH2:48][NH2:49])[O:44][C:43]=2[CH:50]=1>CN(C=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][CH2:13][NH:49][CH2:48][CH:45]2[O:44][C:43]3[CH:50]=[C:39]([O:38][CH3:37])[CH:40]=[CH:41][C:42]=3[O:47][CH2:46]2)=[CH:2]1

参加物

6

反応物 4

HCID 8617Indole-3-Butyric AcidHCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 70200787(S)-7-methoxy-2,3-dihydro-1,4-benzodioxin-2-methanamine hydrochloride

生成物 1

HCID 18923898[4-(1H-Indol-3-yl)-butyl]-(7-methoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)amine収率 63%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

3-Indolebutyric acid (1.3 g, 6.5 mmole), 1-hydroxybenzotriazole hydrate (1.1 g, 7.8 mmole) and 1,3-diisopropylcarbodiimide (2.4 ml, 15.6 mmole) were combined in 100 ml of DMF and stirred at room temperature for 2 hours under a nitrogen atmosphere. To this was added dropwise (S)-7-methoxy-2,3-dihydro-1,4-benzodioxin-2-methanamine hydrochloride (1.5 g, 6.5 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 the eluant. Evaporation of product fractions gave 1.5 g (61%) of the desired product, (S)-(7-methoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-4-(1H-indol-3-yl)-butanamide, as a foam.

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 fractions

出典と根拠

ORDレコード
ord-79d3293c36994725a9b2649cf472b858
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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