Sodium Chloride → HCID 67253910, compound

HRID 453667Notes

Reaction equation

HRID 453667 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:13]=[C:14]([NH:18][C:19](=[O:21])[CH3:20])[CH:15]=[CH:16][CH:17]=2)[C:9]2[C:4](=[CH:5][C:6]([O:24][CH3:25])=[C:7]([O:22][CH3:23])[CH:8]=2)[N:3]=1.O1CCCC1.[CH3:31][NH2:32].[Cl-].[Na+]>C(OCC)(=O)C.CO>[CH3:23][O:22][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[O:24][CH3:25])[N:3]=[C:2]([NH:32][CH3:31])[N:11]=[C:10]2[C:12]1[CH:13]=[C:14]([NH:18][C:19](=[O:21])[CH3:20])[CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6329MethylamineHCID 8028TetrahydrofuranHCID 86654798HCID 86654798, compound

Product 1

HCID 67253910HCID 67253910, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To 353 mg (0.96 mmol) of N-[3-(2-chloro-6,7-dimethoxyquinazolin-4-yl)phenyl]acetamide, tetrahydrofuran (2.06 mL), and methanol (1.03 mL) was added a methanol solution (2.06 mL) of 40% methylamine, and the mixture was reacted at 90° C. for 9 hours. The mixture was allowed to cool and then poured into a mixed solution of ethyl acetate (30 mL) and 5% w/w sodium chloride solution (30 mL) while washing with tetrahydrofuran (30 mL) to extract the organic layer. The organic layer was washed with 5% w/w sodium chloride solution (30 mL) and then concentrated under reduced pressure. To the concentration residue was added t-butyl methyl ether (3 mL), and the mixture was crystallized with a spatula and then suspended by stirring at 50° C. for 2 hours. The mixture was allowed to cool gradually, and then the precipitated crystals were collected by filtration and dried to give 318 mg of a target product (yield: 91.1%).

Workup

  1. customthe mixture was reacted at 90° C. for 9 hours
  2. temperatureto cool
  3. washwhile washing with tetrahydrofuran (30 mL)
  4. extractionto extract the organic layer
  5. washThe organic layer was washed with 5% w/w sodium chloride solution (30 mL)
  6. concentrationconcentrated under reduced pressure
  7. additionTo the concentration residue was added t-butyl methyl ether (3 mL)
  8. customthe mixture was crystallized with a spatula
  9. temperatureto cool gradually
  10. filtrationthe precipitated crystals were collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-98603f64f0d2439ea6f998346c2622d6
Source dataset
uspto-grants-2013_07
Patent number
US08492543B2

Reaction notes

Loading…