Hydrochloric Acid → HCID 59309761, compound

HRID 1513097Notes

Reaction equation

HRID 1513097 reaction equation
[NH2:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([NH:7][C:8](=[O:32])[N:9]2[C:12]2[CH:17]=[C:16]([O:18][CH2:19][C:20]3[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=3[F:28])[C:15]([O:29][CH3:30])=[CH:14][C:13]=2[Cl:31])=[C:5]([O:33][CH3:34])[N:4]=1.N1C=CC=CC=1.[C:41](OC(=O)C)(=[O:43])[CH3:42].Cl>C(Cl)Cl>[C:41]([NH:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([NH:7][C:8](=[O:32])[N:9]2[C:12]2[CH:17]=[C:16]([O:18][CH2:19][C:20]3[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=3[F:28])[C:15]([O:29][CH3:30])=[CH:14][C:13]=2[Cl:31])=[C:5]([O:33][CH3:34])[N:4]=1)(=[O:43])[CH3:42]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 59309806HCID 59309806, compound

Product 1

HCID 59309761HCID 59309761, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-aminomethyl-9-[2-chloro-5-(2-fluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-6-methoxy-7,9-dihydro-8H-purin-8-one (94 mg) and pyridine (0.1 mL) in methylene chloride (3 mL) was added acetic anhydride (0.055 mL), and the mixture was stirred at room temperature for 5 days. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1−ethyl acetate). The obtained product was suspended in diethyl ether, and collected by filtration. The collected material was dried under reduced pressure to give the title compound (44 mg).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1−ethyl acetate)
  6. filtrationcollected by filtration
  7. customThe collected material was dried under reduced pressure

Sources & evidence

ORD record
ord-9cee1e60b0fe4ecfbea18672a10ca65a
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

Loading…