Potassium Carbonate → HCID 58960241, compound

HRID 916478Notes

Reaction equation

HRID 916478 reaction equation
Cl[C:2]1[C:11]2[CH:10]=[C:9]3[O:12][CH2:13][O:14][C:8]3=[CH:7][C:6]=2[N:5]=[CH:4][N:3]=1.[OH:15][C:16]1[CH:17]=[C:18]2[C:22](=[N:23][CH:24]=1)[NH:21][CH:20]=[CH:19]2.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[NH:21]1[C:22]2[C:18](=[CH:17][C:16]([O:15][C:2]3[C:11]4[C:6](=[CH:7][C:8]5[O:14][CH2:13][O:12][C:9]=5[CH:10]=4)[N:5]=[CH:4][N:3]=3)=[CH:24][N:23]=2)[CH:19]=[CH:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 149353678-Chloro-2H-[1,3]dioxolo[4,5-g]quinazolineHCID 220307221H-Pyrrolo[2,3-b]pyridin-5-ol

Product 1

HCID 58960241HCID 58960241, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
85 °C

Procedure

8-Chloro[1,3]dioxolo[4,5-g]quinazoline (100 mg, 0.48 mmol), (WO 9749688), was dissolved in dimethylacetamide (2.5 ml). 5-Hydroxy-7-azaindole (71 mg, 0.53 mmol), (prepared as described for the starting material in Example 2), and potassium carbonate (73 mg, 0.53 mmol) were added and the mixture heated to 85° C. for 3 hours. The reaction mixture was cooled, filtered and concentrated. The resulting residue was purified by column chromatography eluting with methylene chloride/methanol (91/9) to yield 4-(7-azaindol-5-yloxy)-6,7-methylenedioxyquinazoline (92 mg, 63%).

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 (91/9)

Sources & evidence

ORD record
ord-b2afbc792ec743ada0a42bb5cb6d2881
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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