Dimethylformamide → HCID 11088974, compound

HRID 454230Notes

Reaction equation

HRID 454230 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][O:10][C:11]2[CH:20]=[C:19]3[C:14]([C:15](=O)[NH:16][CH:17]=[N:18]3)=[CH:13][C:12]=2[O:22][CH3:23])[CH2:4][CH2:3]1.CN(C=O)C.S(Cl)([Cl:31])=O>>[Cl:31][C:15]1[C:14]2[C:19](=[CH:20][C:11]([O:10][CH2:9][CH2:8][CH:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[C:12]([O:22][CH3:23])[CH:13]=2)[N:18]=[CH:17][N:16]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1354507917-(2-(1-Methylpiperidin-4-yl)ethoxy)-6-methoxy-3,4-dihydroquinazolin-4-one

Product 1

HCID 11088974HCID 11088974, compoundYield 54%

Procedure

A solution of 7-(2-(1-methylpiperidin-4-yl)ethoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (3.1 g, 9.8 mmol) in thionyl chloride (40 ml) containing DMF (400 μl) was refluxed for 4 hours. After cooling, the volatiles were removed under vacuum. The residue was partitioned between methylene chloride and water and the pH of the aqueous layer was adjusted to 11 with solid sodium hydrogen carbonate and aqueous ammonia. The organic layer was separated, dried (MgSO4) and evaporated. The residue was triturated with ether, filtered, washed with ether and dried under vacuum to give 4-chloro-6-methoxy-7-(2-(1-methylpiperidin-4-yl)ethoxy)quinazoline (1.83 g, 54%).

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureAfter cooling
  3. customthe volatiles were removed under vacuum
  4. customThe residue was partitioned between methylene chloride and water
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was triturated with ether
  9. filtrationfiltered
  10. washwashed with ether
  11. customdried under vacuum

Sources & evidence

ORD record
ord-8a85800a5c0040568a9fbe47dc1a5c99
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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