HCID 57546052, compound → HCID 25159651, compound

HRID 913987Notes

Reaction equation

HRID 913987 reaction equation
[C:1]1([C:7]2([CH2:20][O:21][CH2:22][C:23]3[CH:24]=[C:25]([C:32]([F:35])([F:34])[F:33])[CH:26]=[C:27]4[C:31]=3[NH:30][N:29]=[CH:28]4)[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>FC(F)(F)C(O)=O>[C:1]1([C:7]2([CH2:20][O:21][CH2:22][C:23]3[CH:24]=[C:25]([C:32]([F:33])([F:35])[F:34])[CH:26]=[C:27]4[C:31]=3[NH:30][N:29]=[CH:28]4)[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 57546052HCID 57546052, compound

Product 1

HCID 25159651HCID 25159651, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-phenyl-4-(((5-(trifluoromethyl)-1H-indazol-7-yl)methoxy)methyl)piperidine-1-carboxylate (120 mg, 0.245 mmol) was dissolved in trifluoroacetic acid (25% in dichloromethane, 1 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 71 mg (74%). 1H-NMR (CDCl3, 500 MHz) δ 8.04 (s, 1H), 7.92 (s, 1H), 7.45 (m, 2H), 7.32-7.42 (m, 3H), 7.26 (s, 1H), 4.70 (s, 2H), 3.57 (s, 2H), 2.90 (m, 2H), 2.76 (m, 2H), 2.20 (m, 2H), 1.86 (m, 2H); 13C-NMR (CDCl3, 126 MHz) δ 144.1, 139.6, 135.2, 129.0, 127.0, 126.9, 124.7 (q, J=272 Hz), 123.1 (q, J=33 Hz), 122.9, 121.9, 120.3, 118.4, 80.7, 71.8, 50.4, 42.6, 41.7, 33.8. Mass spec.: 390.08 (MH)+. Accurate mass spec.: m/z 390.1801 [MH]+, Δ=2.0 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 71 mg (74%)

Sources & evidence

ORD record
ord-bd15db01453441fcbc2850b908cd1b37
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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