Hydrochloric Acid → HCID 25055217, compound

HRID 1513030Notes

Reaction equation

HRID 1513030 reaction equation
C([O:5][C:6]([C:8]1[N:13]=[C:12]2[N:14]([C:18]3[CH:23]=[C:22]([O:24][CH2:25][C:26]4[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[C:28]([F:34])[C:27]=4[F:35])[C:21]([O:36][CH3:37])=[CH:20][C:19]=3[F:38])[C:15](=[O:17])[NH:16][C:11]2=[CH:10][CH:9]=1)=[O:7])CCC.O1CCCC1.O.[OH-].[Li+].Cl>O.CO>[C:6]([C:8]1[N:13]=[C:12]2[N:14]([C:18]3[CH:23]=[C:22]([O:24][CH2:25][C:26]4[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[C:28]([F:34])[C:27]=4[F:35])[C:21]([O:36][CH3:37])=[CH:20][C:19]=3[F:38])[C:15](=[O:17])[NH:16][C:11]2=[CH:10][CH:9]=1)([OH:7])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68513778HCID 68513778, compound

Product 1

HCID 25055217HCID 25055217, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 5-(n-butoxycarbonyl)-3-[2-fluoro-5-(2,3-difluoro-6-methoxy-benzyloxy)-4-methoxyphenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (0.11 g), tetrahydrofuran (2 mL), methanol (1 mL) and water (1 mL) was added lithium hydroxide monohydrate (43 mg), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was acidified by adding 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with 10% aqueous sodium chloride solution and brine, and dried over anhydrous magnesium 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−ethyl acetate) to give the title compound (23 mg).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with 10% aqueous sodium chloride solution and brine
  3. dry with materialdried over anhydrous magnesium 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−ethyl acetate)

Sources & evidence

ORD record
ord-ffc664f54b2747e6995ec5dfe1d30143
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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