Hydrochloric Acid → HCID 68516489, compound

HRID 1513047Notes

Reaction equation

HRID 1513047 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]2[N:12]([C:16]3[CH:21]=[C:20]([S:22]([N:25]4[C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=5[CH2:29][CH2:28][CH2:27][CH2:26]4)(=[O:24])=[O:23])[C:19]([O:36][CH2:37][CH2:38][O:39][Si](C(C)(C)C)(C)C)=[CH:18][C:17]=3[F:47])[C:13](=[O:15])[NH:14][C:9]2=[C:8]([CH3:48])[CH:7]=1)=[O:5])[CH3:2].[Si](OCCOC1C(S(N2C3C=CC=CC=3CCCC2)(=O)=O)=CC(N)=C(F)C=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]2[N:12]([C:16]3[CH:21]=[C:20]([S:22]([N:25]4[C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=5[CH2:29][CH2:28][CH2:27][CH2:26]4)(=[O:23])=[O:24])[C:19]([O:36][CH2:37][CH2:38][OH:39])=[CH:18][C:17]=3[F:47])[C:13](=[O:15])[NH:14][C:9]2=[C:8]([CH3:48])[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 59309613HCID 59309613, compoundHCID 68515255HCID 68515255, compound

Product 1

HCID 68516489HCID 68516489, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-ethoxycarbonyl-3-{-4-[2-(tert-butyldimethylsilyloxy)-ethoxy]-2-fluoro-5-(2,3,4,5-tetrahydro-1H-1-benzoazepin-1-ylsulfonyl)phenyl}-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (15 mg), which was prepared in a similar manner to that described in Example 40 using 4-[2-(tert-butyldimethylsilyloxy)-ethoxy]-2-fluoro-5-(2,3,4,5-tetrahydro-1H-1-benzoazepin-1-ylsulfonyl)aniline instead of 2-chloro-4-methoxy-5-(1-methyl-1-phenylethylthio)aniline, in tetrahydrofuran (1.5 mL) was added tetra(n-butyl)ammonium fluoride (1 mol/L tetrahydrofuran solution, 0.031 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 magnesium sulfate, and the solvent was removed under reduced pressure to give 5-ethoxycarbonyl-3-[2-fluoro-4-(2-hydroxyethoxy)-5-(2,3,4,5-tetrahydro-1H-1-benzoazepin-1-ylsulfonyl)phenyl]-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (12 mg). The title compound was prepared in a similar manner to that described in Example 43 using this material instead of 3-[2-chloro-4-methoxy-5-(1-methyl-1-phenylethylsulfonyl)phenyl]-5-ethoxycarbonyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one.

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 magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7762fa3a3aba499284f9906b8b367b0e
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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