HCID 57546251, compound → HCID 25159917, compound

HRID 913995Notes

Reaction equation

HRID 913995 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:21][O:22][CH2:23][C:24]3[CH:25]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:27]=[C:28]4[C:32]=3[N:31]([CH3:33])[N:30]=[CH:29]4)[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:21][O:22][CH2:23][C:24]3[CH:25]=[C:26]([C:34]([F:35])([F:36])[F:37])[CH:27]=[C:28]4[C:32]=3[N:31]([CH3:33])[N:30]=[CH:29]4)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 57546251HCID 57546251, compound

Product 1

HCID 25159917HCID 25159917, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(4-fluorophenyl)-4-(((1-methyl-5-(trifluoromethyl)-1H-indazol-7-yl)methoxy)methyl)piperidine-1-carboxylate (66 mg, 0.127 mmol) was dissolved in trifluoroacetic acid (25% in dichloromethane, 2 mL) and stirred at room temperature for 15 min. The reaction was concentrated, and loaded onto a strong cation exchange cartridge in methanol. The cartridge was flushed with several volumes of methanol which were discarded. The product was eluted with 2 M ammonia in methanol and concentrated to give 53.5 mg (100%) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 8.00 (s, 1H), 7.94 (s, 1H), 7.30 (s, 1H), 7.15 (m, 2H), 6.87 (m, 2H), 4.68 (s, 2H), 3.99 (s, 3H), 3.44 (s, 2H), 2.82 (m, 2H), 2.67 (m, 2H), 2.04 (m, 2H), 1.60-1.95 (m, 3H); 13C-NMR (CDCl3, 126 MHz) δ 162.2, 160.2, 139.8, 139.4, 133.9, 128.6, 128.5, 124.8, 124.6 (q, J=272 Hz), 124.5 (q, J=2.9 Hz), 122.6 (q, J=33 Hz), 121.2, 119.7 (q, J=4.8 Hz), 115.0, 114.8, 79.0, 70.5, 42.6, 41.3, 38.3, 33.9. Mass spec.: 422.08 (MH)+. Accurate mass spec.: m/z 422.1837 [MH]+, Δ=4.4 ppm.

Workup

  1. concentrationThe reaction was concentrated
  2. customThe cartridge was flushed with several volumes of methanol which
  3. washThe product was eluted with 2 M ammonia in methanol
  4. concentrationconcentrated
  5. customto give 53.5 mg (100%) as a colorless film

Sources & evidence

ORD record
ord-07b978b8c82a43578d5e3e50875e7a30
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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