Potassium Carbonate → HCID 10173984, compound

HRID 916480Notes

Reaction equation

HRID 916480 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][F:25])[CH2:19][CH2:18]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[OH:26][C:27]1[CH:28]=[C:29]2[C:33](=[N:34][CH:35]=1)[NH:32][CH:31]=[CH:30]2.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[NH:32]1[C:33]2[C:29](=[CH:28][C:27]([O:26][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][N:17]5[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][F:25])[CH2:19][CH2:18]5)=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)=[CH:35][N:34]=2)[CH:30]=[CH:31]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 220307221H-Pyrrolo[2,3-b]pyridin-5-olHCID 589602314-Chloro-7-{2-[4-(2-fluoroethyl)piperazin-1-yl]ethoxy}-6-methoxyquinazoline

Product 1

HCID 10173984HCID 10173984, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
85 °C

Procedure

4-Chloro-7-{2-[4-(2-fluoroethyl)piperazin-1-yl]ethoxy}-6-methoxyquinazoline (172 mg, 0.47 mmol) was dissolved in dimethylacetamide (5 ml). 5-Hydroxy-7-azaindole (69 mg, 0.51 mmol), (prepared as described for the starting material in Example 2), and potassium carbonate (71 mg, 0.51 mmol) were added and the mixture heated to 85° C. for 4 hours. The reaction mixture was cooled, filtered and concentrated. The resulting residue was purified by column chromatography eluting with methylene chloride/methanol (saturated with ammonia) (94/6). The fractions containing the expected product were evaporated under vacuum and the residue was suspended in acetone, filtered and dried under vacuum to give 4-(7-azaindol-5-yloxy)-7-{2-[4-(2-fluoroethyl)piperazin-1-yl]ethoxy}-6-methoxyquinazoline (123 mg, 56%).

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by column chromatography
  6. washeluting with methylene chloride/methanol (saturated with ammonia) (94/6)
  7. additionThe fractions containing the expected product
  8. customwere evaporated under vacuum
  9. filtrationfiltered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-97b97572c6a94a12836e04493db776ff
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

Loading…