Trifluoroacetic acid methylene chloride → HCID 178434308, compound

HRID 914009Notes

Reaction equation

HRID 914009 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[C:6]([CH:15]([O:17][CH2:18][C:19]3([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)[CH3:16])[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=2)[NH:4][N:3]=1.FC(F)(F)C(O)=O.C(Cl)Cl>>[CH3:1][C:2]1[C:10]2[C:5](=[C:6]([CH:15]([O:17][CH2:18][C:19]3([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)[CH3:16])[CH:7]=[C:8]([C:11]([F:13])([F:14])[F:12])[CH:9]=2)[NH:4][N:3]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 178434310HCID 178434310, compound

Product 1

HCID 178434308HCID 178434308, compound

Procedure

(±)-tert-Butyl 4-((1-(3-methyl-5-(trifluoromethyl)-1H-indazol-7-yl)ethoxy)methyl)-4-phenylpiperidine-1-carboxylate (62 mg, 0.12 mmol) was treated with a trifluoroacetic acid/methylene chloride mixture (1:1, 2 mL) for 1 h. The solvent was removed in vacuo and the resulting crude mixture passed through a strong cation exchange column. After washing the column with several volumes of methanol, the product was eluted by washing the column with 2 M ammonia in methanol. The solvent was evaporated to afford 42 mg (77%) as a clear oil. 1H-NMR (CDCl3, 500 MHz) δ 7.82 (s, 1H), 7.37-7.40 (m, 2H), 7.29-7.32 (m, 3H), 7.19 (m, 1H), 4.55 (q, J=6.7 Hz, 1H), 3.41 (q, J=8.9 Hz, 1H), 3.30 (d, J=8.9 Hz, 1H), 2.87-2.93 (m, 2H), 2.68-2.84 (m, 2H), 2.55 (s, 3H), 2.10-2.25 (m, 2H), 1.81-1.93 (m, 2H), 1.42 (m, 3H); 13C-NMR (126 MHz, CDCl3) δ ppm 143.8, 143.6, 139.2, 128.7, 127.3, 127.1, 126.7, 124.9 (q, J=272 Hz), 122.9, 122.4 (q, J=32.6 Hz), 119.8, 117.4, 78.3, 50.5, 42.6, 41.5, 33.5, 22.0, 11.9. Mass spec.: 418.19 (MH)+.

Workup

  1. customThe solvent was removed in vacuo
  2. washAfter washing the column with several volumes of methanol
  3. washthe product was eluted
  4. washby washing the column with 2 M ammonia in methanol
  5. customThe solvent was evaporated
  6. customto afford 42 mg (77%) as a clear oil

Sources & evidence

ORD record
ord-314415eadec74038a3b606a9cc759902
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

Loading…