Dimethylformamide → HCID 59729984, compound

HRID 492540Notes

Reaction equation

HRID 492540 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.CN(C=O)C.CCN(CC)CC.[CH2:33](Br)[CH2:34][CH2:35][CH2:36][CH3:37]>C(OCC)(=O)C>[CH2:33]([N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([O:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][CH:13]=3)[CH:6]=2)[CH2:1]1)[CH2:34][CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80571-BromopentaneHCID 8471TriethylamineHCID 597301424-(1,2,3,4-Tetrahydro-isoquinolin-6-yloxy)-benzamide

Product 1

HCID 59729984HCID 59729984, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 4-(1,2,3,4-tetrahydro-isoquinolin-6-yloxy)-benzamide (80.0 mg, 0.30 mmol), DMF (4 mL), Et3N (0.2 mL, 1.32 mmol), and pentylbromide (0.1 mL, 0.66 mmol) in a 7 mL vial. Place the vial on a shaker at 70° C. for 72 hours and then add ethyl acetate to the reaction vial. Wash with water and several times with 10% LiCl (aq), and dry over Na2SO4. Concentrate the organic mixture and flash chromatograph using 2% 1.0 N NH3 in MeOH, 20% THF, 78% CH2Cl2 to afford 78.0 mg (77% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 0.9-1.0 (3H, m), 1.3-1.4 (4H, m), 1.5-1.7 (2H, m), 2.4-2.6 (2H, m), 2.7-2.8 (2H, m), 2.8-3.0 (2H, m), 3.5-3.6 (2H, m), 6.8-6.8 (2H, m), 6.9-7.1 (3H, m), 7.7-7.9 (2H, m); MS m/z 339 (M+1).

Workup

  1. customat 70° C.
  2. customfor 72 hours
  3. washWash with water and several times with 10% LiCl (aq)
  4. dry with materialdry over Na2SO4
  5. concentrationConcentrate the organic mixture and flash chromatograph

Sources & evidence

ORD record
ord-f52f5408558e4ee8bb6656a43644cfa0
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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