Potassium Carbonate → HCID 69664530, compound

HRID 1791677Notes

Reaction equation

HRID 1791677 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:24](=[O:27])([O-])[O-].[K+].[K+].O[C:31]1[CH:39]=[CH:38][CH:37]=[C:36]2[C:32]=1[CH:33]=C[NH:35]2>CC(N(C)C)=O>[NH:35]1[C:36]2[C:32](=[CH:31][CH:39]=[CH:38][CH:37]=2)[CH:33]=[C:24]1[O:27][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 754211H-indol-4-olHCID 110021914-Chloro-6-methoxy-7-(3-(piperidin-1-YL)propoxy)quinazoline

Product 1

HCID 69664530HCID 69664530, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (200 mg, 0.595 mmol), (prepared as described for the starting material in Example 67), potassium carbonate (411 mg, 2.98 mmol) and 4-hydroxyindole (103 mg, 0.774 mmol) in DMA (2.0 ml) was stirred at 85° C. for 3 hours and allowed to cool to ambient temperature. The reaction mixture was filtered and the filtrate evaporated to give a solid residue. The residue was purified by silica column chromatography, with gradient elution using dichloromethane with 0%, 2%, 4%, 10% methanolic ammonia to give 4-(indolyloxy)-6-methoxy-7-(3-piperidinopropoxy)quinazoline (131 mg, 51%).

Workup

  1. custom(prepared
  2. temperatureto cool to ambient temperature
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate evaporated
  5. customto give a solid residue
  6. customThe residue was purified by silica column chromatography, with gradient elution

Sources & evidence

ORD record
ord-c9267b799df84f46929e357a34a8a5a4
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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