Water → HCID 135788039, compound

HRID 1372986Notes

Reaction equation

HRID 1372986 reaction equation
[OH:1][CH:2]([CH2:18][N:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:15])[NH:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:16][CH3:17].[C:26](OC(=O)C)(=[O:28])[CH3:27].O>CCOCC>[C:26]([O:1][CH:2]([CH2:18][N:19]1[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]1)[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:15])[NH:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:16][CH3:17])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic Anhydride2×HCID 135788038HCID 135788038, compound

Product 1

HCID 135788039HCID 135788039, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 7-[2-hydroxy-3-(4-methylpiperazin-1-yl)propoxy]-6-methoxyquinazolin-4-one (1.2 g, 3.3 mmol) and acetic anhydride (670 μl) in ether (2 ml) was stirred 10 minutes at ambient temperature. Ether (2 ml) was further added, followed by acetic anhydride (670 μl). After stirring 1 hour at ambient temperature, water (305 μl) was added and stirring was continued for 1.5 hours. The mixture was partitioned between methylene chloride and saturated sodium bicarbonate. The organic layer was separated and the aqueous layer was further extracted with methylene chloride. The organic layers were combined, dried (MgSO4) and evaporated. The solid was triturated with ether, filtered, washed with ether and dried under vacuum to give 7-[2-acetoxy-3-(4-methylpiperazin-1-yl)propoxy]-6-methoxyquinazolin-4-one (0.93 g, 72%).

Workup

  1. stirringstirring
  2. waitwas continued for 1.5 hours
  3. customThe mixture was partitioned between methylene chloride and saturated sodium bicarbonate
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was further extracted with methylene chloride
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe solid was triturated with ether
  9. filtrationfiltered
  10. washwashed with ether
  11. customdried under vacuum

Sources & evidence

ORD record
ord-fc202c5140434701b82ac97da6cda164
Source dataset
uspto-grants-2007_01
Patent number
US07160889B2

Reaction notes

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