Hydrochloric Acid → HCID 59309898, compound

HRID 1513058Notes

Reaction equation

HRID 1513058 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:15]=[C:14]2[N:16]([C:20]3[CH:25]=[C:24]([S:26][C:27]([CH3:35])([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH3:28])[C:23]([O:36][CH3:37])=[CH:22][C:21]=3[Cl:38])[C:17](=[O:19])[NH:18][C:13]2=[C:12]([O:39][CH3:40])[CH:11]=1)(C(C)(C)C)(C)C.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>O1CCCC1>[Cl:38][C:21]1[CH:22]=[C:23]([O:36][CH3:37])[C:24]([S:26][C:27]([CH3:35])([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH3:28])=[CH:25][C:20]=1[N:16]1[C:14]2=[N:15][C:10]([CH2:9][OH:8])=[CH:11][C:12]([O:39][CH3:40])=[C:13]2[NH:18][C:17]1=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 59309913HCID 59309913, compound

Product 1

HCID 59309898HCID 59309898, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(tert-butyldimethylsilyloxy)methyl-3-[2-chloro-4-methoxy-5-(1-methyl-1-phenylethylthio)phenyl]-7-methoxy-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (24 mg) in tetrahydrofuran (2 mL) was added tetra(n-butyl)ammonium fluoride hydrate (31 mg), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into 0.5 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with 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=1/1−1/2) to give the title compound (10 mg).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with 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=1/1−1/2)

Sources & evidence

ORD record
ord-3c73c1b77fa942b5b804240c31c2df4e
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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