Trifluoroacetic acid methylene chloride → HCID 25160187, compound

HRID 914004Notes

Reaction equation

HRID 914004 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)[NH:7][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)[NH:7][N:6]=[CH:5]2

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 57545944HCID 57545944, compound

Product 1

HCID 25160187HCID 25160187, compound

Procedure

(±)-tert-Butyl 4-((1-(5-chloro-1H-indazol-7-yl)ethoxy)methyl)-4-phenylpiperidine-1-carboxylate (80 mg, 0.17 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 50 mg (79%) as a clear oil. 1H-NMR (CDCl3, 500 MHz) δ 7.89 (s, 1H), 7.54 (d, J=1.8 Hz, 1H), 7.37-7.40 (m, 2H), 7.30-7.32 (m, 3H), 7.69 (m, 1H), 4.49 (q, J=6.7 Hz, 1H), 3.40 (d, J=9.2 Hz, 1H), 3.29 (d, J=9.2 Hz, 1H), 2.87-2.93 (m, 2H), 2.67-2.77 (m, 2H), 2.07-2.26 (m, 2H), 1.78-1.93 (m, 2H), 1.41 (m, 3H); 13C-NMR (126 MHz, CDCl3) δ ppm 143.7, 135.7, 133.6, 128.8, 127.9, 127.1, 126.7, 126.0, 124.8, 124.1, 118.9, 78.0, 50.4, 42.6, 41.9, 33.5, 22.1. Mass spec.: 370.17 (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 50 mg (79%) as a clear oil

Sources & evidence

ORD record
ord-c39cd2f3c2de4153b380930531c4bb0a
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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