Tetrabutylammonium Fluoride → HCID 59309905, compound

HRID 1513098Notes

Reaction equation

HRID 1513098 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:15]=[C:14]2[N:16]([C:20]3[C:32]([Cl:33])=[CH:31][C:23]([O:24][CH2:25][C:26]([N:28]([CH3:30])[CH3:29])=[O:27])=[C:22]([O:34][CH2:35][C:36]4[C:41]([O:42][CH3:43])=[CH:40][CH:39]=[CH:38][C:37]=4[F:44])[CH:21]=3)[C:17](=[O:19])[NH:18][C:13]2=[C:12]([CH3:45])[CH:11]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[Cl:33][C:32]1[C:20]([N:16]2[C:14]3=[N:15][C:10]([CH2:9][OH:8])=[CH:11][C:12]([CH3:45])=[C:13]3[NH:18][C:17]2=[O:19])=[CH:21][C:22]([O:34][CH2:35][C:36]2[C:41]([O:42][CH3:43])=[CH:40][CH:39]=[CH:38][C:37]=2[F:44])=[C:23]([CH:31]=1)[O:24][CH2:25][C:26]([N:28]([CH3:29])[CH3:30])=[O:27]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59309968HCID 59309968, compound

Product 1

HCID 59309905HCID 59309905, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-{4-[5-(tert-butyldimethylsilyloxy)methyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one-3-yl]-5-chloro-2-(2-fluoro-6-methoxybenzyloxy)phenoxy}-N,N-dimethylacetamide (40 mg) in tetrahydrofuran (0.6 mL) was added tetra(n-butyl)ammonium fluoride (1 mol/L tetrahydrofuran solution, 1.2 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residual solids were suspended in a mixed solvent (n-hexane/ethyl acetate=2/1), and collected by filtration. The collected solids were dried under reduced pressure to give the title compound (16 mg).

Workup

  1. washthe mixture was washed with 1 mol/L hydrochloric acid, water and brine successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. filtrationcollected by filtration
  5. customThe collected solids were dried under reduced pressure

Sources & evidence

ORD record
ord-c38315f54a2b428489194b283c9e93eb
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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