Trifluoroacetic acid → 3-Benzyloxy-8,9,10,11-tetrahydropyrazino[1',2':1,2]imidazo[4,5-c]quinolin-6-amine

HRID 1364064Notes

Reaction equation

HRID 1364064 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[C:18]2[N:19]=[C:20]3[CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22][N:21]3[C:17]=2[C:16]2[C:11](=[CH:12][C:13]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:14][CH:15]=2)[N:10]=1>ClCCl>[CH2:34]([O:33][C:13]1[CH:12]=[C:11]2[C:16]([C:17]3[N:21]4[CH2:22][CH2:23][NH:24][CH2:25][C:20]4=[N:19][C:18]=3[C:9]([NH2:8])=[N:10]2)=[CH:15][CH:14]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66958130tert-butyl 6-amino-3-benzyloxy-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

Product 1

HCID 669581223-Benzyloxy-8,9,10,11-tetrahydropyrazino[1',2':1,2]imidazo[4,5-c]quinolin-6-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 mL of a 10% solution in dichloromethane) was added to tert-butyl 6-amino-3-benzyloxy-10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate (0.550 g, 1.23 mmol), and the reaction was stirred at ambient temperature overnight. The solvent was removed under reduced pressure, and the residue was treated with hydrogen chloride (4 N in 1,4-dioxane). The solvent was removed under reduced pressure, and the residue was dissolved in methanol. Ammonia gas was bubbled through the resulting solution for 15 minutes, and then the solvent was removed under reduced pressure. The residue was dried overnight under vacuum to provide 3-benzyloxy-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine in a crude mixture, which was used in the next step without purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was treated with hydrogen chloride (4 N in 1,4-dioxane)
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in methanol
  5. customAmmonia gas was bubbled through the resulting solution for 15 minutes
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was dried overnight under vacuum

Sources & evidence

ORD record
ord-de218d13b4e746c09b3d46dedd9e263f
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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