Trifluoroacetic acid → 2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethaneamine

HRID 47502

Reaction equation

HRID 47502 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[C:18]2[N:19]=[C:20]([CH2:32][CH2:33][CH2:34][CH3:35])[N:21]([CH2:22][CH2:23][NH:24]C(=O)OC(C)(C)C)[C:17]=2[C:16]2[N:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1>ClCCl>[NH2:8][C:9]1[C:18]2[N:19]=[C:20]([CH2:32][CH2:33][CH2:34][CH3:35])[N:21]([CH2:22][CH2:23][NH2:24])[C:17]=2[C:16]2[N:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 221727511,1-dimethylethyl N-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]carbamate

Product 1

HCID 219460272-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethaneamineYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of 1,1-dimethylethyl N-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]carbamate (5.7 g, 15 mmol) in dichloromethane (10 mL). The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was diluted with dichloromethane and then extracted with 10% hydrochloric acid. The hydrochloric acid extract was washed twice with dichloromethane and then it was made basic with ammonium hydroxide. The resulting precipitate was isolated by filtration and dried to provide 3.7 g of 2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethaneamine as a white powder, m.p. 175-176° C. Analysis: Calculated for C15H20N6: %C, 63.36; %H, 7.09; %N, 29.55. Found: %C, 62.98; %H, 6.92; %N, 29.89. HRMS (EI) calcd for C15H20N6 (M+) 284.1749, found 284.1748.

Workup

  1. extractionextracted with 10% hydrochloric acid
  2. extractionThe hydrochloric acid extract
  3. washwas washed twice with dichloromethane
  4. customThe resulting precipitate was isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-a516dfd25ec14edcb269af2d046b14a5
Source dataset
uspto-grants-2004_03
Patent number
US06699878B2

Linked notes

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