Hydrochloric Acid → HCID 71147595, compound

HRID 578816Notes

Reaction equation

HRID 578816 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]2[C:14]=1[C:13](=[O:15])[N:12]([C:16]1[CH:21]=[C:20]([O:22][CH2:23][C:24]3[C:29]([O:30][CH2:31][CH2:32][OH:33])=[CH:28][CH:27]=[C:26]([F:34])[C:25]=3[F:35])[CH:19]=[CH:18][C:17]=1[F:36])[C:11](=[O:37])[NH:10]2)=[O:5])[CH3:2].N1C=CC=CC=1.Cl[C:45]([O:47][CH2:48][CH3:49])=[O:46].Cl>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]2[C:14]=1[C:13](=[O:15])[N:12]([C:16]1[CH:21]=[C:20]([O:22][CH2:23][C:24]3[C:29]([O:30][CH2:31][CH2:32][O:33][C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:28][CH:27]=[C:26]([F:34])[C:25]=3[F:35])[CH:19]=[CH:18][C:17]=1[F:36])[C:11](=[O:37])[NH:10]2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10928Ethyl chloroformateHCID 68992889HCID 68992889, compound

Product 1

HCID 71147595HCID 71147595, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 5-ethoxycarbonyl-3-{2-fluoro-5-[2,3-difluoro-6-(2-hydroxyethoxy)benzyloxy]phenyl}thieno[3,4-d]-pyrimidine-2,4(1H,3H)-dione (80 mg) in ethyl acetate (2 mL) were added pyridine (0.036 mL) and ethyl chloroformate (0.021 mL), and the mixture was stirred at room temperature overnight. 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=1/2) to give the title compound (38 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=1/2)

Sources & evidence

ORD record
ord-be54b06962764028902af9baba9b9171
Source dataset
uspto-grants-2015_05
Patent number
US09040693B2

Reaction notes

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