Trifluoroacetic acid → HCID 66665793, compound

HRID 406216Notes

Reaction equation

HRID 406216 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[CH2:22][CH2:21][CH2:20][N:19]([CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([C:7]2[N:8]=[C:9]3[CH2:22][CH2:21][CH2:20][N:19]([CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][C:29]([OH:31])=[O:30])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86681850HCID 86681850, compound

Product 1

HCID 66665793HCID 66665793, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-(4-(2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)butoxy)acetate (step 4)(20 mg, 0.042 mmol) in DCM (0.5 ml) was treated with TFA (0.5 ml, 6.49 mmol) and stirred at RT for 1 h. The solvent was removed in vacuo and the crude product was dissolved in DCM (with <10% MeOH) and basified with saturated sodium bicarbonate solution. The organic portion was separated and the aqueous was extracted with 10% MeOH/DCM. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound;

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe crude product was dissolved in DCM (with <10% MeOH)
  3. customThe organic portion was separated
  4. extractionthe aqueous was extracted with 10% MeOH/DCM
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d0fcd352c8a46edaefc7b088dcf4218
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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