Trifluoroacetic acid methylene chloride → HCID 25160188, compound

HRID 914007Notes

Reaction equation

HRID 914007 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](C)[N:6]=[CH:5]2.F[C:36](F)(F)C(O)=O.C(Cl)Cl>>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([O:13][CH2:14][C:15]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH3:12])[C:8]2[C:4](=[CH:5][N:6]([CH3:36])[N:7]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 57546219HCID 57546219, compound

Product 1

HCID 25160188HCID 25160188, compound

Procedure

(±)-tert-Butyl 4-((1-(5-chloro-1-methyl-1H-indazol-7-yl)ethoxy)methyl)-4-phenylpiperidine-1-carboxylate (27 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 18 mg (79%) as a clear oil. 1H-NMR (CDCl3, 500 MHz) δ 7.86 (s, 1H), 7.54 (d, J=1.8 Hz, 1H), 7.28-7.32 (m, 4H), 7.19-7.23 (m, 1H), 7.10 (d, J=1.8 Hz, 1H), 4.74 (q, J=6.4 Hz, 1H), 3.97 (s, 3H), 3.36 (d, J=9.2 Hz, 1H), 3.23 (d, J=9.2 Hz, 1H), 2.87-2.89 (m, 2H), 2.70-2.76 (m, 2H), 2.13-2.16 (m, 2H), 1.83-1.90 (m, 2H), 1.44 (d, J=6.4 Hz, 3H); 13C-NMR (126 MHz, CDCl3) δ ppm 144.1, 136.3, 132.5, 128.4, 128.3, 127.2, 126.8, 126.2, 126.1, 125.2, 119.4, 78.2, 42.7, 41.8, 39.9, 33.6, 33.4, 23.4. 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 18 mg (79%) as a clear oil

Sources & evidence

ORD record
ord-95e6d0ca41c844a39a5facf516aafa08
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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