Iodoethane → N-cyclopropyl-3-[7-[(1-ethylpiperidin-4-yl)oxy]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzamide

HRID 506978Notes

Reaction equation

HRID 506978 reaction equation
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([O:23][CH:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)=[CH:18][CH:19]=4)[C:14]3=[O:30])[CH:7]=2)[CH2:3][CH2:2]1.I[CH2:33][CH3:34].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([O:23][CH:24]5[CH2:29][CH2:28][N:27]([CH2:33][CH3:34])[CH2:26][CH2:25]5)=[CH:18][CH:19]=4)[C:14]3=[O:30])[CH:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 67018601N-Cyclopropyl-4-methyl-3-[1-oxo-7-(piperidin-4-yloxy)isoquinolin-2(1H)-yl]benzamide

Product 1

HCID 11647987N-cyclopropyl-3-[7-[(1-ethylpiperidin-4-yl)oxy]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Cyclopropyl-4-methyl-3-[1-oxo-7-(piperidin-4-yloxy)isoquinolin-2(1H)-yl]benzamide (50 mg), iodoethane (0.105 ml) and potassium carbonate (66 mg) were stirred in DMF (0.5 ml) at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with water (5×), brine, dried (magnesium sulfate) and concentrated to give N-cyclopropyl-3-[7-[(1-ethylpiperidin-4-yl)oxy]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzamide as a cream coloured foam solid (44 mg); NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 1.00 (t, 3H), 1.69 (m, 2H), 1.99 (m, 2H), 2.10 (s, 3H), 2.25 (m, 2H), 2.38 (m, 2H), 2.71 (m, 2H), 2.85 (m, 1H), 4.53 (m, 1H), 6.70 (d, 1H), 7.20 (d, 1H), 7.41 (d, 1H), 7.49 (d, 1H), 7.67 (s, 1H), 7.70 (d, 1H), 7.72 (s, 1H), 7.88 (d, 1H), 8.42 (d, 1H); Mass Spectrum: M+H+ 446.

Workup

  1. washwashed with water (5×), brine
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e92657012ffd4ad59694841e9599f064
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

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