Potassium Iodide → HCID 67018589, compound

HRID 507000Notes

Reaction equation

HRID 507000 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([CH3:29])=[CH:10][N:11]([C:16]3[CH:17]=[C:18]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:19]([NH:21][CH:22]3[CH2:24][CH2:23]3)=[O:20])[C:12]2=[O:15])=[CH:7][CH:6]=1.BrCCOC1C=C2C(C(C)=[CH:39][N:40]([C:45]3[CH:46]=C(C=C[C:56]=3C)C(NC3CC3)=O)C2=O)=CC=1.[I-].[K+].CNC(C)C>CC(N(C)C)=O.C(OCC)(=O)C>[CH:22]1([NH:21][C:19](=[O:20])[C:18]2[CH:25]=[CH:26][C:27]([CH3:28])=[C:16]([N:11]3[CH:10]=[C:9]([CH3:29])[C:8]4[C:13](=[CH:14][C:5]([O:4][CH2:3][CH2:2][N:40]([CH:45]([CH3:46])[CH3:56])[CH3:39])=[CH:6][CH:7]=4)[C:12]3=[O:15])[CH:17]=2)[CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 78485N-MethylisopropylamineHCID 67018572HCID 67018572, compoundHCID 67018588HCID 67018588, compound

Product 1

HCID 67018589HCID 67018589, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-[7-(2-chloroethoxy)-4-methyl-1-oxoisoquinolin-2(1H)-yl]-N-cyclopropyl-4-methylbenzamide and 3-[7-(2-bromoethoxy)-4-methyl-1-oxoisoquinolin-2(1H)-yl]-N-cyclopropyl-4-methylbenzamide (4:1, 225 mg), potassium iodide (182 mg), and N-methylisopropylamine (0.34 ml) 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 N-cyclopropyl-3-[7-{2-[isopropyl(methyl)amino]ethoxy}-4-methyl-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzamide (105 mg) as a pale yellow foam; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 0.97 (d, 6H), 2.10 (s, 3H), 2.24 (s, 3H), 2.27 (s, 3H), 2.76 (t, 2H), 2.80-2.89 (m, 2H), 4.14 (m, 2H), 7.09 (s, 1H), 7.45-7.51 (m, 2H), 7.70-7.75 (m, 3H), 7.86 (d, 1H), 8.45 (d, 1H); Mass Spectrum: M+H+ 448.

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-6113b0ba0a8543198e2cf16cfa2a8ee1
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

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