Cesium carbonate → HCID 58960257, compound

HRID 2068096Notes

Reaction equation

HRID 2068096 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:15]=[C:16]3[C:21](=[CH:22][C:23]=2[O:24][CH3:25])[N:20]=[CH:19][N:18]=[C:17]3Cl)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[OH:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][N:32]=[CH:31]2.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][C:23]=2[O:24][CH3:25])[N:20]=[CH:19][N:18]=[C:17]3[O:27][C:28]2[CH:29]=[C:30]3[C:34](=[CH:35][CH:36]=2)[NH:33][N:32]=[CH:31]3)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1014381H-Indazol-5-olHCID 58960248HCID 58960248, compound

Product 1

HCID 58960257HCID 58960257, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-[3-(4-acetylpiperazin-1-yl)propoxy]-4-chloro-7-methoxyquinazoline (235 mg, 0.62 mmol), 5-hydroxyindazole (100 mg, 0.75 mmol), (prepared as described for the starting material in Example 29), and cesium carbonate (303 mg, 0.93 mmol) in acetone (20 ml) was heated at reflux for 2 hours. The mixture was filtered and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 6-[3-(4-acetylpiperazin-1-yl)propoxy]-4-(1H-indazol-5-yloxy)-7-methoxyquinazoline (200 mg, 68%) as a pale green solid.

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 2 hours
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washeluting with methylene chloride/methanol (95/5)

Sources & evidence

ORD record
ord-b62f304668814fca9bdde8e74405ced1
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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