6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline → HCID 178418719, compound

HRID 8713

Reaction equation

HRID 8713 reaction equation
Cl[C:2]1[NH:3][S:4](=[O:17])(=[O:16])[C:5]2[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:6]=2[N:7]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][C:29]=1[O:30][CH3:31])[CH2:26][NH:25][CH2:24][CH2:23]2>COC(O)C>[CH3:18][O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][C:29]=1[O:30][CH3:31])[CH2:26][N:25]([C:2]1[NH:3][S:4](=[O:17])(=[O:16])[C:5]3[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:6]=3[N:7]=1)[CH2:24][CH2:23]2

Participants

4

Reactant 2

HCID 156236,7-Dimethoxy-1,2,3,4-TetrahydroisoquinolineHCID 178418955HCID 178418955, compound

Product 1

HCID 178418719HCID 178418719, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Procedure

3-Chloro-6,7-dimethoxy-2H-benzo[1,2,4]thiadiazine-1,1-dioxide 1a (154 mg, 0.55 mmol) and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 2a (wherein R1 and R4 are hydrogen, and R2 and R3 are methoxy) (138 mg, 0.6 mmol) were dissolved in 20 ml of methoxyethanol and heated at reflux for 72 h. The solvent was removed under reduced pressure. The gummy residue was triturated with isopropanol and the resulting crystals filtered. Recrystallization from dichloromethane afforded 120 mg of 3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-6,7-dimethoxy-2H-benzo[1,2,4]thiadiazine-1,1-dioxide 101, [M+H]+=434.

Workup

  1. temperatureheated
  2. temperatureat reflux for 72 h
  3. customThe solvent was removed under reduced pressure
  4. customThe gummy residue was triturated with isopropanol
  5. filtrationthe resulting crystals filtered
  6. customRecrystallization from dichloromethane

Sources & evidence

ORD record
ord-3ea103740d49442d947174854bfe2809
Source dataset
uspto-grants-2006_08
Patent number
US07091200B2

Linked notes

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