Potassium Carbonate → HCID 22030869, compound

HRID 1791780Notes

Reaction equation

HRID 1791780 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][C:17]([CH3:22])=[CH:16]4)=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:23][CH3:24].C(=O)([O-])[O-].[K+].[K+].[CH3:31][N:32]1[CH2:37][CH2:36][CH:35]([CH2:38]C2(S([O-])(=O)=O)C=CC(C)=CC2)[CH2:34][C:33]1=[O:50]>CN(C=O)C.CC(C)=O>[CH3:24][O:23][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[O:1][CH2:38][CH:35]1[CH2:36][CH2:37][N:32]([CH3:31])[C:33](=[O:50])[CH2:34]1)[N:9]=[CH:8][N:7]=[C:6]2[O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH3:22])=[CH:16]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 86602438HCID 86602438, compoundHCID 1357631087-hydroxy-6-methoxy-4-(2-methyl-1H-indol-5-yloxy)quinazoline

Product 1

HCID 22030869HCID 22030869, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (280 mg, 0.87 mmol), (prepared as described in Example 49), potassium carbonate (370 mg, 2.68 mmol) and 4-(1-methyl-2-oxopiperidin-4-yl)methyl-4-toluene sulphonate (260 mg, 0.87 mmol) in DMF (8 ml) was stirred at 95° C. for 4 hours and allowed to cool to ambient temperature. The reaction mixture was diluted with acetone, filtered and the filtrate evaporated ‘in vacuo’ to give a residue which was purified by column chromatography, eluting with dichloromethane/methanol/0.88 ammonia (100/8/1). The relevant fractions were combined and evaporated ‘in vacuo’ to give an oil which crystallised on trituration with diethyl ether to give 6-methoxy-4-(2-methylindol-5-yloxy)-7-(1-methyl-2-oxopiperidin-4-ylmethoxy)quinazoline (66 mg, 17%).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered
  3. customthe filtrate evaporated ‘in vacuo’
  4. customto give a residue which
  5. customwas purified by column chromatography
  6. washeluting with dichloromethane/methanol/0.88 ammonia (100/8/1)
  7. customevaporated ‘in vacuo’
  8. customto give an oil which
  9. customcrystallised on trituration with diethyl ether

Sources & evidence

ORD record
ord-b48f576b22e64091bd7a8f6512fa62ec
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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