Trifluoroacetic acid → HCID 10120551, compound

HRID 2229207Notes

Reaction equation

HRID 2229207 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)[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].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl.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[CH2:11][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]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 22091442HCID 22091442, compound

Product 1

HCID 10120551HCID 10120551, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 58 mg (0.1 mmol) of N-({3-[(2,5-dimethoxyphenyl) hydroxymethyl](imidazolo[1,2-a]pyridin-2-yl)}methyl)(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide in 5 mL dichloromethane is treated with 116 mg (1.0 mmol) triethylsilane and 114 mg (1.0 mmol) trifluoroacetic acid. The solution is heated in a sealed tube at 60° C. for 18 hr and diluted with 15 mL sat. NaHCO3 and extracted with 3×10 mL dichloromethane. The combined organics are washed with 10 mL water and 10 mL brine. The resulting organic layer is dried over anhydrous MgSO4 and the solvent removed in vacuo to give the crude material. The residue is prep-plate chromatographed (9% MeOH/CH2Cl2/0.5% NH4OH) to afford 33 mg (58%) N-({3-[(2,5-dimethoxyphenyl)methyl](imidazolo[1,2-a]pyridin-2-yl)}methyl)(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide. Mass Spec m/z (M++1) 567.

Workup

  1. extractionextracted with 3×10 mL dichloromethane
  2. washThe combined organics are washed with 10 mL water and 10 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. customThe residue is prep-plate chromatographed (9% MeOH/CH2Cl2/0.5% NH4OH)

Sources & evidence

ORD record
ord-e28a692b971d4cf7a4166a9266692ec4
Source dataset
uspto-grants-2002_07
Patent number
US06420365B1

Reaction notes

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