Trifluoroacetic acid → HCID 67477379, compound

HRID 454932Notes

Reaction equation

HRID 454932 reaction equation
F[C:2](F)(F)C(O)=O.[N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[N:18]1[CH2:23][CH2:22][CH:21]([O:24][C:25]2[C:26]([CH:31]3[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]3)=N[CH:28]=[CH:29][N:30]=2)[CH2:20][CH2:19]1>C(Cl)Cl>[NH:34]1[CH2:33][CH2:32][CH:31]([C:26]2[C:25]([O:24][CH:21]3[CH2:20][CH2:19][N:18]([C:9]4[CH:10]=[CH:11][C:16]5[C:17](=[CH:12][CH:13]=[CH:14][CH:15]=5)[N:8]=4)[CH2:23][CH2:22]3)=[N:30][CH:29]=[CH:28][CH:2]=2)[CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58547873HCID 58547873, compound

Product 1

HCID 67477379HCID 67477379, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.272 mL, 3.53 mmol) was added to a solution of tert-butyl 4-(3-(1-(quinolin-2-yl)piperidin-4-yloxy)pyrazin-2-yl)piperidine-1-carboxylate (1726 mg, 3.53 mmol) in DCM (2 mL) and stirred at RT until the starting material was completely consumed. The mixture was then diluted with ethyl acetate and neutralized with saturated aqueous sodium bicarbonate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered and concentrated. The brown solid was triturated with acetone and dried to give the title compound as a white solid (370 mg, 27% yield). [M+1] 390.2. IC50 (uM) 0.05444. 1H NMR (CDCl3, 400 MHz) δ (ppm): 1.53-1.69 (m, 1H) 1.86-2.00 (m, 2H) 2.12-2.34 (m, 6H) 3.03-3.14 (m, 2H) 3.23-3.32 (m, 1H) 3.53-3.71 (m, 4H) 4.13-4.22 (m, 2H) 5.35-5.43 (m, 1H) 7.06 (d, J=9.19 Hz, 1H) 7.20-7.26 (m, 1H) 7.52-7.59 (m, 1H) 7.62 (d, J=7.82 Hz, 1H) 7.67-7.82 (m, 1H) 7.89-7.95 (m, 1H) 7.97 (d, J=2.74 Hz, 1H) 8.06 (d, J=2.74 Hz, 1H)

Workup

  1. customwas completely consumed
  2. additionThe mixture was then diluted with ethyl acetate and neutralized with saturated aqueous sodium bicarbonate
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organics were washed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe brown solid was triturated with acetone
  10. customdried

Sources & evidence

ORD record
ord-6b2ff9544e5e44779f0605b3a2bbd338
Source dataset
uspto-grants-2013_07
Patent number
US08497265B2

Reaction notes

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