Dimethylformamide → HCID 44434063, compound

HRID 130932Notes

Reaction equation

HRID 130932 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][N: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][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(OCC)(=O)C.O>[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][N:13]=3)[CH:6]=2)[CH2:1]1)[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7666Phenethyl bromideHCID 8471TriethylamineHCID 59730015HCID 59730015, compound

Product 1

HCID 44434063HCID 44434063, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 6-(1,2,3,4-tetrahydro-isoquinolin-6-yloxy)-nicotinamide (46.9 mg, 0.17 mmol), DMF (3 mL), Et3N (0.1 mL, 0.77 mmol), and phenethylbromide (52 uL, 0.38 mmol) in a 7 mL vial. Place the reaction vial on a shaker at 70° C. for 72 hours, and then add water and ethyl acetate. Wash the ethyl acetate layer several times with water, 10% LiCl, and dry over Na2SO4. Concentrate organic mixture and flash chromatograph using 30% THF, 4% 1.0 N NH3 in MeOH, 76% CH2Cl2 to afford 23.2 mg, (37% yield) of the title compound: MS m/z 374 (M+1).

Workup

  1. customthe reaction vial on a shaker at 70° C. for 72 hours
  2. washWash the ethyl acetate layer several times with water, 10% LiCl
  3. dry with materialdry over Na2SO4

Sources & evidence

ORD record
ord-59d875db52ff45f29c0450928a30193c
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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