Trifluoroacetic acid → HCID 57546222, compound

HRID 913960Notes

Reaction equation

HRID 913960 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:21][O:22][CH:23]([C:25]3[CH:26]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:28]=[C:29]4[C:33]=3[NH:32][C:31](=[O:34])[CH2:30]4)[CH3:24])[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:21][O:22][CH:23]([C:25]3[CH:26]=[C:27]([C:35]([F:37])([F:36])[F:38])[CH:28]=[C:29]4[C:33]=3[NH:32][C:31](=[O:34])[CH2:30]4)[CH3:24])[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57546196HCID 57546196, compound

Product 1

HCID 57546222HCID 57546222, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-fluorophenyl)-4-((1-(2-oxo-5-(trifluoromethyl)indolin-7-yl)ethoxy)methyl)piperidine-1-carboxylate (13 mg, 0.024 mmol) in dichloromethane (1.5 mL) at ice bath temperature was added TFA (200 μL, 2.60 mmol). The mixture was stirred at this temperature for 1 hour. TLC (30% ethyl acetate/hexanes) indicated complete conversion of starting material. The mixture was concentrated and the crude residue was loaded onto an SCX cartridge (Phenomenex Strata X-C 200mg) with methanol then the resin was washed with methanol and the compound eluted with 2N NH3 in methanol to give the product (10.2 mg, 0.023 mmol, 96%) as a clear pale yellow film. 1H-NMR (CDCl3, 400 MHz) δ 7.57-7.88 (m, 1H), 7.32 (s, 1H), 7.21-7.29 (m, 2H), 7.11 (s, 1H), 7.03 (t, J=8.69 Hz, 2H), 4.28 (q, J=6.55 Hz, 1H), 3.42 (s, 2H), 3.31-3.36 (m, 1H), 3.24-3.30 (m, 1H), 2.83-2.96 (m, 2H), 2.63-2.80 (m, 2H), 2.17 (ddd, J=13.72, 2.27 Hz, 1H), 2.06 (dt, J=13.60, 2.27 Hz, 1H), 1.74-1.91 (m, 2H), 1.29 (d, J=6.55 Hz, 3H). Mass spec. (M-H)−: 435.5, (MH)+: 437.3.

Workup

  1. concentrationThe mixture was concentrated
  2. washthe resin was washed with methanol
  3. washthe compound eluted with 2N NH3 in methanol

Sources & evidence

ORD record
ord-32fe9c9f5415472383d4c38c17142076
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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