HCID 57546205, compound → HCID 25159783, compound

HRID 913990Notes

Reaction equation

HRID 913990 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([C:5]([CH2:15][O:16][CH2:17][C:18]3([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)=[CH:6][C:7]([C:11]([F:14])([F:13])[F:12])=[CH:8]2)=[N:3]1>FC(F)(F)C(O)=O>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([C:5]([CH2:15][O:16][CH2:17][C:18]3([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]3)=[CH:6][C:7]([C:11]([F:12])([F:14])[F:13])=[CH:8]2)=[N:3]1

Participants

3

Reactant 1

HCID 57546205HCID 57546205, compound

Product 1

HCID 25159783HCID 25159783, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(((2-methyl-5-(trifluoromethyl)-2H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (76 mg, 0.151 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 64 mg (quant.) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 7.94 (s, 1H), 7.84 (s, 1H), 7.41 (m, 2H), 7.34 (m, 2H), 7.28 (s, 1H), 7.21 (m, 1H), 4.83 (s, 2H), 4.18 (s, 3H), 3.57 (s, 2H), 2.90 (m, 2H), 2.76 (m, 2H), 2.20 (m, 2H), 1.95 (m, 2H), 1.85 (bs, 1H); 13C-NMR (CDCl3, 126 MHz) δ 147.6, 144.4, 129.4, 128.3, 127.3, 126.1, 125.5, 124.9 (q, J=272 Hz), 124.2 (q, J=32 Hz), 120.7, 118.7, 117.5 (q, J=4.8 Hz), 80.2, 68.7, 42.9, 42.0, 40.7, 33.7. Mass spec.: 404.10 (MH)+. Accurate mass spec.: m/z 404.1936 [MH]+, Δ=3.4 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 64 mg (quant.) as a colorless film

Sources & evidence

ORD record
ord-c52e2c98467b4b73a8e8034ca47e2886
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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