Acetic Anhydride → HCID 21260325, compound

HRID 634654Notes

Reaction equation

HRID 634654 reaction equation
C(N(CC)CC)C.[C:8]([O:11][C:12](=[O:14])[CH3:13])(=O)[CH3:9].Cl.[CH2:16]([O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([NH:34][C:35]3C=C(O)[C:38]([Cl:42])=[CH:37][C:36]=3[F:43])=[N:29][CH:30]=[N:31]2)=[CH:26][C:25]=1[O:44][CH3:45])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[C:12]([O:11][C:8]1[C:38]([Cl:42])=[CH:37][C:36]([F:43])=[C:35]([CH:9]=1)[NH:34][C:28]1[C:27]2[C:32](=[CH:33][C:24]([O:23][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[C:25]([O:44][CH3:45])[CH:26]=2)[N:31]=[CH:30][N:29]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22624880HCID 22624880, compound

Product 1

HCID 21260325HCID 21260325, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (216 ml, 1.5 mmol) and then acetic anhydride (133 ml, 1.4 mmol) were added to a stirred suspension of 7-benzyloxy-4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxy quinazoline hydrochloride (600 mg, 1.4 mmol) in methylene chloride (7 ml). The mixture was stirred at ambient temperature for 3 hours and insoluble material removed by filtration. Volatiles were removed from the filtrate by evaporation and the residue purified by flash chromatography eluting with methylene chloride/methanol (100/0 increasing in polarity to 97/3) to give 4-(5-acetoxy-4-chloro-2-fluoroanilino)-7-benzyloxy-6-methoxyquinazoline (340 mg, 52%) as a solid.

Workup

  1. custominsoluble material removed by filtration
  2. customVolatiles were removed from the filtrate by evaporation
  3. customthe residue purified by flash chromatography
  4. washeluting with methylene chloride/methanol (100/0 increasing in polarity to 97/3)

Sources & evidence

ORD record
ord-0e5f4d7f05204817aa755fb07eaa20d5
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

Loading…