Sodium hydride → HCID 9907179, compound

HRID 1597203Notes

Reaction equation

HRID 1597203 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH2:3][C:2]1=[O:10].[H-].[Na+].Cl[C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:26][CH2:27][CH2:28][O:29][CH3:30])=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][N:15]=1>C1COCC1.CN(C=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:26][CH2:27][CH2:28][O:29][CH3:30])=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)[C:2]1=[O:10]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 107306534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazolineHCID 138640951,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-one

Product 1

HCID 9907179HCID 9907179, compoundYield 151.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 7-azaoxindole (268 mg, 2 mmol) in THF (3 ml) was added to a suspension of sodium hydride (80 mg, 2 mmol, prewashed with THF) in THF (4 ml). After stirring for 20 minutes at ambient temperature a solution of 4-chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline (180 mg, 0.7 mmol) in a mixture of THF (3 ml) and DMF (1 ml) was added. After stirring for 30 minutes at ambient temperature followed by 1 hour at 65° C., the volatiles were removed by evaporation. The residue was partitioned between water and ether. The aqueous layer was separated and adjusted to pH4 with 2M hydrochloric acid. The precipitate was collected by filtration and dried under vacuum, it was then suspended in methylene chloride/methanol (1/1) and 3M hydrogen chloride in ether was added. The solid was collected by filtration, washed with methanol followed by ether and dried under vacuum to give 4-(7-azaoxindol-3-yl)-6-methoxy-7-(2-methoxyethoxy)quinazoline (388 mg, 68%).

Workup

  1. additionwas added
  2. waitfollowed by 1 hour at 65° C.
  3. customthe volatiles were removed by evaporation
  4. customThe residue was partitioned between water and ether
  5. customThe aqueous layer was separated
  6. filtrationThe precipitate was collected by filtration
  7. customdried under vacuum, it
  8. addition3M hydrogen chloride in ether was added
  9. filtrationThe solid was collected by filtration
  10. washwashed with methanol
  11. customdried under vacuum

Sources & evidence

ORD record
ord-43aba99d04f44643aeadad1a4141246d
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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