Dichloromethane → HCID 70657317, compound

HRID 69009Notes

Reaction equation

HRID 69009 reaction equation
[C:1]([Cl:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10]CCl.Cl.Cl.Cl.[CH3:16][NH:17][CH2:18][CH2:19][N:20]([CH2:36][C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1)[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[C:31](=[O:35])[NH:30][CH2:29][CH2:28]2.C(OC(=O)C)C.Cl>C(OCC)(=O)C.O.C(N(CC)CC)C>[ClH:9].[ClH:10].[CH3:16][N:17]([CH2:18][CH2:19][N:20]([CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[C:31](=[O:35])[NH:30][CH2:29][CH2:28]2)[CH2:36][C:37]1[CH:38]=[CH:39][N:40]=[CH:41][CH:42]=1)[C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 21866389Hydrogen chloride-ethyl acetateHCID 669612116-{3-[(2-methylaminoethyl)pyridin-4-ylmethylamino]propoxy}-3,4-dihydro-2H-isoquinolin-1-one trihydrochloride

Product 1

HCID 70657317HCID 70657317, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzoyl chloride (0.14 ml) was added to a dichloromethane solution (10 ml) of 6-{3-[(2-methylaminoethyl)pyridin-4-ylmethylamino]propoxy}-3,4-dihydro-2H-isoquinolin-1-one trihydrochloride (382 mg), and triethylamine (0.56 ml) under ice cooling. The mixture was stirred at room temperature overnight. Water was added to the reaction mixture, followed by extraction using dichloromethane. The organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1→4:1). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride ethyl acetate solution (0.28 ml) was added to an ethyl acetate solution (10 ml) of the residue. The precipitated insoluble matter was separated, washed with ethyl acetate, and dried to give the title compound (242 mg) as a white powder.

Workup

  1. extractionfollowed by extraction
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1→4:1)
  4. customcondensed under reduced pressure
  5. customThe precipitated insoluble matter was separated
  6. washwashed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-aaf8078a35424846abf5875d3a31f039
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

Loading…