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

HRID 1290254

반응식

HRID 1290254 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-57ac7f372d1141ed8f33c4cf7fbe130c
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750724

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