Pyridine → 1-methyl-1H-pyrazole-3-sulfonic acid benzyl-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-amide

HRID 1947638

Reaktionsgleichung

Reaktionsgleichung von HRID 1947638
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[NH:14][CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:26][N:27]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[N:28]1>C(#N)C>[CH2:1]([N:8]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[NH:14][CH2:13][CH2:12]2)[S:32]([C:29]1[CH:30]=[CH:31][N:27]([CH3:26])[N:28]=1)(=[O:34])=[O:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 134744661-Methyl-1H-pyrazole-3-sulfonyl chlorideHCID 672239156-benzylamino-3,4-dihydro-2H-isoquinolin-1-one

Produkt 1

HCID 672239981-methyl-1H-pyrazole-3-sulfonic acid benzyl-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-amideAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a stirred solution of 6-benzylamino-3,4-dihydro-2H-isoquinolin-1-one (45 mg, 0.18 mmol) and pyridine (31 μl, 0.39 mmol) in anhydrous acetonitrile (1 ml) was added 1-methyl-1H-pyrazole-3-sulfonyl chloride (70 mg, 0.39 mmol) and the reaction heated to 150° C. in a microwave for 0.5 hrs. The solvent was evaporated in vacuo and the crude residue purified by preparative tlc (5% methanol in dichloromethane) to afford the title compound as a yellow solid (10 mg, 14%). HPLC retention time 3.83 min. Mass spectrum (ES+) m/z 397 (M+H).

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customthe crude residue purified by preparative tlc (5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-c56c91d3a32c4bb49b4d22546a0e637f
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399481B2

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