Trifluoroacetic acid methylene chloride → HCID 25160186, compound

HRID 914006Notes

Reaction equation

HRID 914006 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]([O:13][CH2:14][C:15]3([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)[CH3:12])[CH:10]=1)[N:7]([CH3:34])[N:6]=[CH:5]2.FC(F)(F)C(O)=O.C(Cl)Cl>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]([O:13][CH2:14][C:15]3([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]3)[CH3:12])[CH:10]=1)[N:7]([CH3:34])[N:6]=[CH:5]2

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 57546219HCID 57546219, compound

Product 1

HCID 25160186HCID 25160186, compound

Procedure

(±)-tert-Butyl 4-((1-(5-chloro-1-methyl-1H-indazol-7-yl)ethoxy)methyl)-4-phenylpiperidine-1-carboxylate (22 mg, 0.06 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 17 mg (97%) as a clear oil. 1H-NMR (CDCl3, 500 MHz) δ 7.78 (s, 1H), 7.44 (d, J=1.8 Hz, 1H), 7.31-7.37 (m, 4H), 7.20-7.23 (m, 1H), 6.89 (m, 1H), 4.91 (q, J=6.4 Hz, 1H), 4.16 (s, 3H), 3.40 (d, J=9.2 Hz, 1H), 3.35 (d, J=9.2 Hz, 1H), 2.89-2.95 (m, 2H), 2.71-2.79 (m, 2H), 2.12-2.20 (m, 2H), 1.94-2.03 (m, 2H), 1.44 (d, J=6.4 Hz, 3H); 13C-NMR (126 MHz, CDCl3) δ ppm 145.7, 144.3, 135.4, 128.3, 127.8, 127.3, 126.1, 123.2, 122.7, 122.4, 117.1, 78.4, 74.0, 42.8, 42.0, 40.5, 33.4, 22.6. Mass spec.: 384.17 (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 17 mg (97%) as a clear oil

Sources & evidence

ORD record
ord-de3cf8eacf86485ebe58b231e348eab1
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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