Potassium Carbonate → HCID 10217396, compound

HRID 916389Notes

Reaction equation

HRID 916389 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18](Cl)=[N:19][CH:20]=[N:21]3)=[CH:16][C:15]=2[O:25][CH3:26])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[OH:27][C:28]1[CH:29]=[C:30]2[C:34](=[N:35][CH:36]=1)[NH:33][CH:32]=[CH:31]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18]([O:27][C:28]4[CH:29]=[C:30]5[C:34](=[N:35][CH:36]=4)[NH:33][CH:32]=[CH:31]5)=[N:19][CH:20]=[N:21]3)=[CH:16][C:15]=2[O:25][CH3:26])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 220307221H-Pyrrolo[2,3-b]pyridin-5-olHCID 589602297-(3-(4-Acetylpiperazin-1-yl)propoxy)-4-chloro-6-methoxyquinazoline

Product 1

HCID 10217396HCID 10217396, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A solution of 7-(3-(4-acetylpiperazin-1-yl)propoxy)-4-chloro-6-methoxyquinazoline (0.285 g, 0.753 mmol), 5-hydroxy-7-azaindole (0.111 g, 0.828 mmol), (prepared as described for the starting material in Example 2), and potassium carbonate (0.114 g, 0.828 mmol) in DMF (1.6 ml) was stirred and heated at 95° C. under nitrogen for 3 hours. The mixture was cooled and filtered and the filtrate was evaporated. The residue was purified by column chromatography eluting with increasingly polar mixtures of methylene chloride and methanol (saturated with ammonia). The fractions containing the expected product were combined and evaporated and the residue was triturated under diethyl ether, filtered and dried under vacuum to give 7-(3-(4-acetylpiperazin-1-yl)propoxy)-4-(7-azaindol-5-yloxy)-6-methoxyquinazoline (0.225 g, 62%).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column chromatography
  5. washeluting
  6. temperaturewith increasingly polar mixtures of methylene chloride and methanol (saturated with ammonia)
  7. additionThe fractions containing the expected product
  8. customevaporated
  9. customthe residue was triturated under diethyl ether
  10. filtrationfiltered
  11. customdried under vacuum

Sources & evidence

ORD record
ord-b4d600e84a8b4b85b121205da9f67f68
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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