Trifluoroacetic acid → 4-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butylamine

HRID 11345Notes

Reaction equation

HRID 11345 reaction equation
[CH3:1][C:2]1[N:3]([CH2:20][CH2:21][CH2:22][CH2:23][NH:24]C(=O)OC(C)(C)C)[C:4]2[C:9]([CH3:10])=[C:8]([CH3:11])[N:7]=[C:6]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:5]=2[N:19]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[CH3:1][C:2]1[N:3]([CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[C:4]2[C:9]([CH3:10])=[C:8]([CH3:11])[N:7]=[C:6]([O:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:5]=2[N:19]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 12109127tert-butyl 4-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butylcarbamate

Product 1

HCID 121091284-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butylamineYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of tert-butyl 4-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butylcarbamate (6.70 g, 15.8 mmol) in dichloromethane (50 mL) was slowly added to a chilled (0° C.) mixture of trifluoroacetic acid (60 mL) and dichloromethane (100 mL). The reaction mixture was allowed to warm to ambient temperature and then left overnight. The reaction mixture was concentrated under reduced pressure to provide a brown oil. The oil was dissolved in dichloromethane and the solution was made basic (pH 14) with 5% aqueous sodium hydroxide. The layers were separated and the aqueous layer was extracted with dichloromethane. The organic layers were combined, dried over magnesium sulfate and then concentrated under reduced pressure to provide 4.50 g of 4-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butylamine as a brown oil.

Workup

  1. temperaturea chilled
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto provide a brown oil
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with dichloromethane
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81371807103f44619e2687ec592562bd
Source dataset
uspto-grants-2006_08
Patent number
US07098221B2

Reaction notes

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