Trifluoroacetic acid → HCID 68920940, compound

HRID 1845731Notes

Reaction equation

HRID 1845731 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][CH2:11][C:12]1[N:13]([CH2:25][C:26]([NH:29][C:30](=[O:44])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH:36]C(=O)OC(C)(C)C)([CH3:28])[CH3:27])[C:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:24]=1)[CH3:9]>ClCCl.O.[OH-].[NH4+]>[NH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][C:30]([NH:29][C:26]([CH3:27])([CH3:28])[CH2:25][N:13]1[C:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:24]=[C:12]1[CH2:11][O:10][CH2:8][CH3:9])=[O:44]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68929484HCID 68929484, compound

Product 1

HCID 68920940HCID 68920940, compoundYield 105.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 14923Ammonium HydroxideSolvent

Procedure

Trifluoroacetic acid (30 mL) was added slowly to a solution of tert-butyl 6-({2-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}amino)-6-oxohexylcarbamate (3.99 g, 7.82 mmol) in dichloromethane (80 mL) at room temperature. After 1.5 hours, the solution was concentrated under reduced pressure to afford an oil. The oil was dissolved in a small amount of water and concentrated ammonium hydroxide. The resulting basic mixture was extracted with dichloromethane multiple times. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 3.4 g of 6-amino-N-{2-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}hexanamide, which was used in the next step without further purification.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. customto afford an oil
  3. extractionThe resulting basic mixture was extracted with dichloromethane multiple times
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9452b846bb94715b6fecd9deb85d518
Source dataset
uspto-grants-2015_02
Patent number
US08951528B2

Reaction notes

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