Potassium Iodide → HCID 66919140, compound

HRID 2354210Notes

Reaction equation

HRID 2354210 reaction equation
ClC(C)COO[C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][N:10]([C:16]1[CH:17]=[C:18]([CH:25]=[CH:26][C:27]=1[CH3:28])[C:19]([NH:21][CH:22]1[CH2:24][CH2:23]1)=[O:20])[C:9]2=[O:29].[NH:31]1[CH2:36][CH2:35][S:34][CH2:33][CH2:32]1.[I-].[K+]>CC(N(C)C)=O>[CH:22]1([NH:21][C:19](=[O:20])[C:18]2[CH:25]=[CH:26][C:27]([CH3:28])=[C:16]([N:10]3[C:9](=[O:29])[C:8]4[C:13](=[CH:14][CH:15]=[C:6]([O:20][CH2:19][CH2:18][CH2:17][N:31]5[CH2:36][CH2:35][S:34][CH2:33][CH2:32]5)[CH:7]=4)[N:12]=[CH:11]3)[CH:17]=2)[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 67164ThiomorpholineHCID 86610963HCID 86610963, compound

Product 1

HCID 66919140HCID 66919140, compoundYield 147.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

3-[6-(2-Chloropropoxyoxy)-4-oxoquinazolin-3(4H)-yl]-N-cyclopropyl-4-methylbenzamide (0.23 g), thiomorpholine (0.37 g) and potassium iodide (0.2 g) were stirred in DMA (3 ml) and heated under microwave irradiation conditions (Personal Chemistry Emrys Optimizer with 300 W magnetron) for 30 mins at 120° C. The reaction mixture was filtered, washed with ethyl acetate and the filtrate concentrated. Purification by column chromatography on a silica column eluting with a 0% to 30% MeOH/EtOAc gradient gave the title compound (0.19 g) as a white solid; Mass Spectrum: M+H+ 479.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with ethyl acetate
  3. concentrationthe filtrate concentrated
  4. customPurification by column chromatography on a silica column
  5. washeluting with a 0% to 30% MeOH/EtOAc gradient

Sources & evidence

ORD record
ord-dd97540fb04948a19d3fd219038dd198
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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