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Potassium Carbonate → 4-(4-Chloroquinolin-7-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazoline

HRID 1791568
Notes
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Reaction equation

HRID 1791568 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][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:24][C:25]1[C:34]2[C:29](=[CH:30][C:31]([OH:35])=[CH:32][CH:33]=2)[N:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:24][C:25]1[C:34]2[C:29](=[CH:30][C:31]([O:35][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]5[CH2:23][CH2:22][O:21][CH2:20][CH2:19]5)=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)=[CH:32][CH:33]=2)[N:28]=[CH:27][CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolineHCID 1357290834-Chloroquinolin-7-ol2×

Product 1

HCID 98913554-(4-Chloroquinolin-7-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazolineYield 47%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
100 °C

Procedure

To 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (250 mg, 0.74 mmol), (prepared as described for the starting material in Example 1), in suspension in DMF (4 ml) were successively added 4-chloro-7-hydroxyquinoline (133 mg, 0.74 mmol) and potassium carbonate (153 mg, 1 mmol) and the reaction mixture heated to 100° C. More 4-chloro-7hydroxyquinoline (27 mg, 0.15 mmol) was added after one hour and heating was continued for a further 30 minutes. The product precipitated upon cooling to ambient temperature. The reaction mixture was diluted with water, the product was collected by filtration and washed with more water. The dried solid was triturated with ether and filtered to give 4-(4-chloroquinolin-7-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazoline (166 mg, 47%).

Workup

  1. temperatureheating
  2. customThe product precipitated
  3. temperatureupon cooling to ambient temperature
  4. additionThe reaction mixture was diluted with water
  5. filtrationthe product was collected by filtration
  6. washwashed with more water
  7. customThe dried solid was triturated with ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-ab7b8d70f4d6495f995fc35087a3a344
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07074800B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes