HCID 57545954, compound → HCID 25159782, compound

HRID 913989Notes

Reaction equation

HRID 913989 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:33]([F:36])([F:35])[F:34])=[CH:8][C:9]=2[CH2:11][O:12][CH2:13][C:14]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)[CH:4]=[N:3]1>FC(F)(F)C(O)=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:33]([F:36])([F:35])[F:34])=[CH:8][C:9]=2[CH2:11][O:12][CH2:13][C:14]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)[CH:4]=[N:3]1

Participants

3

Reactant 1

HCID 57545954HCID 57545954, compound

Product 1

HCID 25159782HCID 25159782, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(((1-methyl-5-(trifluoromethyl)-1H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (187 mg, 0.371 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 151 mg (quant.) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 7.97 (s, 1H), 7.92 (s, 1H), 7.31 (s, 1H), 7.21 (m, 4H), 7.14 (m, 1H), 4.64 (s, 2H), 3.90 (s, 3H), 3.46 (s, 2H), 2.82 (m, 2H), 2.69 (m, 2H), 2.09 (m, 2H), 1.79 (m, 2H), 1.60 (bs, 1H); 13C-NMR (CDCl3, 126 MHz) δ 144.2, 139.5, 133.8, 128.3, 127.1, 126.2, 124.8, 124.7 (q, J=272 Hz), 124.5, 122.5 (q, J=33 Hz), 121.3, 119.6 (q, J=4.8 Hz), 79.4, 70.6, 42.7, 41.7, 38.2, 33.8. Mass spec.: 404.14 (MH)+. Accurate mass spec.: m/z 404.1947 [MH]+, Δ=0.7 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 to 151 mg (quant.) as a colorless film

Sources & evidence

ORD record
ord-8aded5c36bfc447683679673e1bf6836
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

Loading…