Trifluoroacetic acid → HCID 9929975, compound

HRID 1452671Notes

Reaction equation

HRID 1452671 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[NH:21][C:22](=[O:35])[CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34].FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[CH:4][C:3]=1[NH:21][C:22](=[O:35])[CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57526948HCID 57526948, compound

Product 1

HCID 9929975HCID 9929975, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of tert-butyl 4-(4-fluoro-3-{[5-(2-methoxyphenyl)pentanoyl]amino}phenyl)-1-piperidinecarboxylate (48.4 mg, 0.100 mmol) in CH2Cl2 (2.0 mL) was added trifluoroacetic acid (114 mg, 1.0 mmol) at room temperature. The reaction mixture was stirred for 30 min and concentrated in vacuo. The residue was dissolved in CHCl3/i-PrOH (3:1, 10 mL) and was basified to pH 11 with 5% KOH solution. The organic layer was separated and the aqueous layer was extracted with CHCl3/i-PrOH (3:1, 3×10 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford afford N-[2-fluoro-5-(4-piperidinyl)phenyl]-5-(2-methoxyphenyl)pentanamide (38.0 mg, 95%): 1H NMR (400 MHz, CD3OD) δ 8.30-8.12 (m, 1H), 7.64-7.41 (m, 1H), 7.24-7.07 (m, 2H), 7.06-6.92 (m, 1H), 6.92-6.74 (m, 3H), 3.80 (s, 3H), 3.25-3.06 (m, 2H), 2.80-2.49 (m, 5H), 2.48-2.24 (m, 3H), 1.89-1.71 (m, 4H), 1.71-1.46 (m, 4H); ESMS m/e: 385.2 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in CHCl3/i-PrOH (3:1, 10 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CHCl3/i-PrOH (3:1, 3×10 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto afford

Sources & evidence

ORD record
ord-f47dc56e7765467fb2b8fe7da5eb515d
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

Loading…