Hydrochloric Acid → 3-{3-[(7-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-amino]-propyl}-1H-indol-5-ol

HRID 1290252노트

반응식

HRID 1290252 반응식
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][CH2:19][C:20](O)=O)C1C=CC=CC=1.O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.Cl.[CH3:44][O:45][C:46]1[CH:47]=[CH:48][C:49]2[O:54][CH2:53][CH:52]([CH2:55][NH2:56])[O:51][C:50]=2[CH:57]=1.Cl>CN(C=O)C>[CH3:44][O:45][C:46]1[CH:47]=[CH:48][C:49]2[O:54][CH2:53][CH:52]([CH2:55][NH:56][CH2:20][CH2:19][CH2:18][C:12]3[C:11]4[C:15](=[CH:16][CH:17]=[C:9]([OH:8])[CH:10]=4)[NH:14][CH:13]=3)[O:51][C:50]=2[CH:57]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 189238737-Methoxy-2,3-dihydro-1,4-benzodioxin-2-methanamine hydrochlorideHCID 189238923-[5-(Benzyloxy)-3-indolyl]propanoic Acid

생성물 1

HCID 189239093-{3-[(7-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-amino]-propyl}-1H-indol-5-ol수율 90%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

5-Benzyloxyindole-3-propionic acid (1.8 g, 6.0 mmole), 1-hydroxybenzotriazole hydrate (0.97 g, 7.2 mmole) and 1,3-diisopropylcarbodiimide (2.3 ml, 14.4 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 (1.4 g, 6.0 hydrochloride (1.4 g, 6.0 mmole) in 50 ml of DMF and the mixture was further stirred for 48 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 using first dichloromethane and then 2.5% methanol in dichloromethane as eluants to give 2.6 g (90%) of the desired product, (7-methoxy-2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-(5-benzyloxy-1H-indol-3-yl)-propanamide, as a light tan solid.

후처리

  1. stirringthe mixture was further stirred for 48 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 using first dichloromethane

출처 및 근거

ORD 기록
ord-7e7720cfc5e24f2fa9b4d6078814227e
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750724

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