Trifluoroacetic acid → 4-(5-(6-(Piperazin-1-yl)pyridin-3-yl)-2-((quinolin-2-yloxy)methyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

HRID 1772688Notes

Reaction equation

HRID 1772688 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:32]=[C:33]([CH2:35][O:36][C:37]4[CH:46]=[CH:45][C:44]5[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=5)[N:38]=4)[N:34]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([N:19]4[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]4)=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO.C(Cl)Cl>[N:19]1([C:16]2[N:17]=[CH:18][C:13]([C:10]3[N:9]4[CH:32]=[C:33]([CH2:35][O:36][C:37]5[CH:46]=[CH:45][C:44]6[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=6)[N:38]=5)[N:34]=[C:8]4[C:7]([N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)=[N:12][CH:11]=3)=[CH:14][CH:15]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86345944HCID 86345944, compound

Product 1

HCID 863457724-(5-(6-(Piperazin-1-yl)pyridin-3-yl)-2-((quinolin-2-yloxy)methyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of compound 47a (144 mg, 0.240 mmol) in DCM (1 mL) was added TFA (0.8 mL). The resulting mixture was stirred at rt for 1 h and concentrated under reduced pressure. The residue obtained was dried under reduced pressure overnight, suspended in 20 mL of diethyl ether, sonicated for 5 min and concentrated. The solid obtained was dried under reduced pressure for 4 h to obtain a residue which was dissolved in 1:1 MeOH/DCM solution (5 mL) and filtered through a sodium bicarbonate cartridge. The filtrate was concentrated under reduced pressure and the resulting residue was triturated in ether to give compound 47b. Mass Spectrum (LCMS, ESI pos.) Calcd. for C29H30N8O2: 523.2 (M+H). Found 523.3.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. customwas dried under reduced pressure overnight
  4. customsonicated for 5 min
  5. concentrationconcentrated
  6. customThe solid obtained
  7. customwas dried under reduced pressure for 4 h
  8. customto obtain a residue which
  9. filtrationfiltered through a sodium bicarbonate cartridge
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customthe resulting residue was triturated in ether

Sources & evidence

ORD record
ord-28d18c60abb84e0dbfa94be230c110b8
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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