Hydrochloric Acid → HCID 66960533, compound

HRID 69012Notes

Reaction equation

HRID 69012 reaction equation
Br[C:2]1[CH:32]=[CH:31][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH2:11][CH2:12][N:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])=[CH:4][CH:3]=1.[NH:33]1[CH2:37][CH2:36][CH2:35][C:34]1=[O:38].C(=O)([O-])[O-].[K+].[K+].CNCCNC.[ClH:51]>[Cu](I)I.C(O)C.C1(C)C=CC=CC=1>[ClH:51].[ClH:51].[O:38]=[C:34]1[CH2:35][CH2:36][CH2:37][N:33]1[C:2]1[CH:32]=[CH:31][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH2:11][CH2:12][N:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 669599672-(2-{[3-(4-Bromophenoxy)propyl]pyridin-4-ylmethylamino}ethyl)-2H-isoquinolin-1-one

Product 1

HCID 66960533HCID 66960533, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

2-(2-{[3-(4-Bromophenoxy)propyl]pyridin-4-ylmethylamino}ethyl)-2H-isoquinolin-1-one (500 mg), 2-pyrrolidone (0.228 ml), potassium carbonate (415 mg), copper iodide (I)(190 mg), and N,N′-dimethyl ethylenediamine (0.39 ml) were added to toluene (5 ml). The mixture was stirred at 100° C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature. After adding aqueous ammonia, extraction was performed using ethyl acetate. The organic layer was washed with saturated saline, and dried with sodium sulfate. After the organic layer was condensed under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:0,70:30). The purified product was condensed under reduced pressure. A condensed hydrochloric acid (0.3 ml) was added to an ethanol solution of the residue, followed by condensation under reduced pressure. The residue was recrystallized from isopropyl alcohol/water to give the title compound (350 mg) as a white powder. mp: 210 to 214° C. (dec.)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionAfter adding aqueous
  3. extractionammonia, extraction
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried with sodium sulfate
  6. customcondensed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:0,70:30)
  8. customcondensed under reduced pressure
  9. customfollowed by condensation under reduced pressure
  10. customThe residue was recrystallized from isopropyl alcohol/water

Sources & evidence

ORD record
ord-00cc7d72754a4c8b8cae090396375e20
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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