Potassium Carbonate → HCID 22030838, compound

HRID 1791832Notes

Reaction equation

HRID 1791832 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.[OH:24][C:25]1[CH:26]=[C:27]2[CH:33]=[CH:32][NH:31][C:28]2=[N:29][CH:30]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CN(C=O)C.ClCCl.CO>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[N:5]=[CH:4][N:3]=[C:2]2[O:24][C:25]1[CH:26]=[C:27]2[CH:33]=[CH:32][NH:31][C:28]2=[N:29][CH:30]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 110021914-Chloro-6-methoxy-7-(3-(piperidin-1-YL)propoxy)quinazolineHCID 220307221H-Pyrrolo[2,3-b]pyridin-5-ol

Product 1

HCID 22030838HCID 22030838, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (227 mg, 0.68 mmol), (prepared as described for the starting material in Example 67), 5-hydroxy-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.75 mmol), (prepared as described for the starting material in Example 182), and potassium carbonate (350 mg, 2.5 mmol) in DMF (4 ml) was stirred at 95° C. for 6 hours and allowed to cool to ambient temperature. The reaction mixture was treated with 1.0 N aqueous sodium hydroxide solution and allowed to stir at ambient temperature for a few minutes. The resulting precipitate was filtered off, washed with water and air dried to give a crude product. This was purified by column chromatography, eluting initially with dichloromethane/methanol (85/15) to isolate a less polar impurity and then with dichloromethane/methanol/0.88 ammonia (100/8/1) to isolate the target compound. The relevant fractions were combined and evaporated in vacuo to give a white solid which was triturated with acetone, filtered and dried to give 6-methoxy-7-(3-piperidinopropoxy)4-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)quinazoline (58 mg, 20%).

Workup

  1. custom(prepared
  2. custom(prepared
  3. temperatureto cool to ambient temperature
  4. stirringto stir at ambient temperature for a few minutes
  5. filtrationThe resulting precipitate was filtered off
  6. washwashed with water and air
  7. customdried
  8. customto give a crude product
  9. customThis was purified by column chromatography
  10. washeluting initially with dichloromethane/methanol (85/15)
  11. customto isolate a less polar impurity
  12. customevaporated in vacuo
  13. customto give a white solid which
  14. customwas triturated with acetone
  15. filtrationfiltered
  16. customdried

Sources & evidence

ORD record
ord-52ecf86f5b8543e4b0f31151b76f850e
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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