Trifluoroacetic acid → HCID 24963987, compound

HRID 600289Notes

Reaction equation

HRID 600289 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:39]=[CH:38][C:12]3[N:13]=[C:14]([N:24]4[CH2:29][CH2:28][N:27]([CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])[CH2:26][CH2:25]4)[C:15](=[O:23])[N:16]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH3:22])[C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:39]=[CH:38][C:12]3[N:13]=[C:14]([N:24]4[CH2:25][CH2:26][N:27]([CH2:30][C:31]([OH:33])=[O:32])[CH2:28][CH2:29]4)[C:15](=[O:23])[N:16]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH3:22])[C:11]=3[CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58993881HCID 58993881, compound

Product 1

HCID 24963987HCID 24963987, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl {4-[7-(6-methoxypyridin-3-yl)-2-oxo-1-(2-propoxyethyl)-1,2-dihydropyrido[3,4-b]pyrazin-3-yl]piperazin1-yl}acetate (174 mg, 0.32 mmol) in dichloromethane (3 mL) was treated with trifluoroacetic acid (2 mL) and stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, triturated with diethyl ether, concentrated and recrystallized from ethyl acetate and hexane and filtered. The {4-[7-(6-methoxypyridin-3-yl)-2-oxo-1-(2-propoxyethyl)-1,2-dihydropyrido[3,4-b]pyrazin-3-yl]piperazin1-yl}acetic acid was obtained as a white solid. (81 mg, 52% yield).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customtriturated with diethyl ether
  3. concentrationconcentrated
  4. customrecrystallized from ethyl acetate and hexane
  5. filtrationfiltered

Sources & evidence

ORD record
ord-827dacdba9d24911bb18ac7e4bbcfc09
Source dataset
uspto-grants-2011_03
Patent number
US07902195B2

Reaction notes

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