HCID 57546206, compound → HCID 25159787, compound

HRID 913996Notes

Reaction equation

HRID 913996 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[C:32]4[C:28](=[CH:29][N:30]([CH3:33])[N:31]=4)[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=3)[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[C:32]4[C:28](=[CH:29][N:30]([CH3:33])[N:31]=4)[CH:27]=[C:26]([C:34]([F:35])([F:36])[F:37])[CH:25]=3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 57546206HCID 57546206, compound

Product 1

HCID 25159787HCID 25159787, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(4-fluorophenyl)-4-(((2-methyl-5-(trifluoromethyl)-2H-indazol-7-yl)methoxy)methyl)piperidine-1-carboxylate (26 mg, 0.050 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 20.6 mg (98%) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 7.98 (s, 1H), 7.86 (s, 1H), 7.35 (m, 2H), 7.23 (s, 1H), 7.00 (m, 2H), 4.82 (s, 2H), 4.21 (s, 3H), 3.54 (s, 2H), 2.90 (m, 2H), 2.74 (m, 2H), 2.14 (m, 2H), 1.60-2.05 (m, 3H); 13C-NMR (CDCl3, 126 MHz) δ 162.3, 160.3, 147.6, 140.2, 129.2, 128.9, 128.8, 125.6, 124.9 (q, J=272 Hz), 124.2 (q, J=32 Hz), 120.8, 118.8 (q, J=2.9 Hz), 117.6 (q, J=5.8 Hz), 115.0, 114.9, 79.9, 68.7, 42.7, 41.6, 40.7, 33.9. Mass spec.: 422.12 (MH)+. Accurate mass spec.: m/z 422.1836 [MH]+, Δ=4.6 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 20.6 mg (98%) as a colorless film

Sources & evidence

ORD record
ord-7be76ebcb48c48eea18e5407fe9f1683
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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