Fluoride Ion → HCID 22091442, compound

HRID 2229206Notes

Reaction equation

HRID 2229206 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]([O:41][Si](C)(C)C(C)(C)C)[C:12]1[N:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]2=[N:14][C:13]=1[CH2:21][N:22]([CH2:36][CH2:37][CH:38]([CH3:40])[CH3:39])[C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[C:26]=1[Cl:35])=[O:24].[F-]>C1COCC1.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]([OH:41])[C:12]1[N:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]2=[N:14][C:13]=1[CH2:21][N:22]([CH2:36][CH2:37][CH:38]([CH3:39])[CH3:40])[C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[C:26]=1[Cl:35])=[O:24]

Participants

5

Reactant 2

HCID 28179Fluoride IonHCID 22091441HCID 22091441, compound

Product 1

HCID 22091442HCID 22091442, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 390 mg (0.56 mmol) of N-({3-[(2,5-dimethoxyphenyl) (1,1,2,2-tetramethyl-1-silapropoxy)methyl](imidazolo[1,2-a]pyridin-2-yl)}methyl) (2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide in 12 mL THF is treated with 0.70 mL (0.7 mmol) 1M tetabutylammonium fluoride in THF. The mixture is stirred at room temperature for 1 hr, diluted with 15 mL sat. NaHCO3 and extracted with 3×15 mL ether. The combined organics are washed with 25 mL water and 25 mL brine. The resulting organic layer is dried over anhydrous MgSO4 and the solvent removed in vacuo to give the crude material. A small sample of the residue is prep-plate chromatographed (9% MeOH/CH2Cl2/0.5% NH4OH) to afford N-({3-[(2,5-dimethoxyphenyl)hydroxymethyl](imidazolo[1,2-a]pyridin-2-yl)}methyl)(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide. Mass Spec m/z (M++1) 584.

Workup

  1. extractionextracted with 3×15 mL ether
  2. washThe combined organics are washed with 25 mL water and 25 mL brine
  3. dry with materialThe resulting organic layer is dried over anhydrous MgSO4
  4. customthe solvent removed in vacuo
  5. customto give the crude material
  6. customA small sample of the residue is prep-plate chromatographed (9% MeOH/CH2Cl2/0.5% NH4OH)

Sources & evidence

ORD record
ord-32cd2312dda643e197df37767ac7394c
Source dataset
uspto-grants-2002_07
Patent number
US06420365B1

Reaction notes

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