Potassium Iodide → HCID 11676151, compound

HRID 507012Notes

Reaction equation

HRID 507012 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][N:11]([C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][C:26]=3[CH3:27])[C:19]([NH:21][CH2:22][CH3:23])=[O:20])[C:12]2=[O:15])=[CH:7][CH:6]=1.[I-].[K+].[CH3:30][NH:31][CH:32]([CH3:34])[CH3:33]>CC(N(C)C)=O.C(OCC)(=O)C>[CH:32]([N:31]([CH3:30])[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][N:11]([C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][C:26]=3[CH3:27])[C:19]([NH:21][CH2:22][CH3:23])=[O:20])[C:12]2=[O:15])=[CH:7][CH:6]=1)([CH3:34])[CH3:33]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 78485N-MethylisopropylamineHCID 67018573HCID 67018573, compound

Product 1

HCID 11676151HCID 11676151, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

3-[7-(2-Chloroethoxy)-1-oxoisoquinolin-2(1H)-yl]-N-ethyl-4-methylbenzamide (150 mg), potassium iodide (129 mg) and methylisopropylamine (244 μL, 2.34 mmol) were stirred in DMA (3 ml) and heated under microwave irradiation conditions (Personal Chemistry Emrys Optimizer with 300 W magnetron) at 150° C. for 1 hour. The reaction mixture was diluted with ethyl acetate and washed with water (×5), brine (×2), dried (magnesium sulfate) and concentrated. Purification by column chromatography on a silica column eluting using initially 10% methanol/ethyl acetate and then a 99:1 mixture of 10% methanol/ethyl acetate and aqueous ammonia solution gave 3-[7-[2-(Isopropylmethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-N-ethyl-4-methylbenzamide as a foam (104 mg); NMR Spectrum: (DMSO d6) 0.97 (d, 6H), 1.12 (t, 3H), 2.11 (s, 3H), 2.23 (s, 3H), 2.75 (t, 2H), 2.83 (m, 1H), 3.29 (m, 2H), 4.13 (m, 2H), 6.73 (d, 1H), 7.23 (d, 1H), 7.41 (m, 1H), 7.51 (d, 1H), 7.67 (d, 1H), 7.72 (d, 1H), 7.78 (d, 1H), 7.89 (m, 1H), 8.51 (t, 1H); Mass Spectrum: M+H+ 422.

Workup

  1. washwashed with water (×5), brine (×2)
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated
  4. customPurification by column chromatography on a silica column
  5. washeluting
  6. additiona 99:1 mixture of 10% methanol/ethyl acetate and aqueous ammonia solution

Sources & evidence

ORD record
ord-1a3017676a14460b8e97c1cb58deb94b
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

Loading…