HCID 57546124, compound → HCID 25159524, compound

HRID 913986Notes

Reaction equation

HRID 913986 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([C:5]([CH2:12][O:13][CH2:14][C:15]3([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[CH:6][C:7]([CH3:11])=[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]([CH2:12][O:13][CH2:14][C:15]3([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]3)=[CH:6][C:7]([CH3:11])=[CH:8]2)=[N:3]1

Participants

3

Reactant 1

HCID 57546124HCID 57546124, compound

Product 1

HCID 25159524HCID 25159524, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(((2,5-dimethyl-2H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (8 mg, 0.018 mmol) was dissolved in trifluoroacetic acid (25% in dichloromethane, 1.5 mL) and stirred at room temperature for 45 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 to give 6.8 mg (quant.) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 7.73 (s, 1H), 7.41 (m, 2H), 7.35 (m, 2H), 7.22 (m, 2H), 6.84 (s, 1H), 4.82 (s, 2H), 4.15 (s, 3H), 3.54 (s, 2H), 2.91 (m, 2H), 2.75 (m, 2H), 2.33 (s, 3H), 2.18 (m, 2H), 1.98 (m, 2H), 1.50-2.30 (bs, 1H); 13C-NMR (CDCl3, 126 MHz) δ 146.3, 144.6, 131.1, 128.3, 127.4, 127.3, 126.0, 125.7, 122.8, 122.5, 116.9, 79.8, 69.1, 42.8, 42.0, 40.3, 33.5, 21.9. Mass spec.: 350.04 (MH)+. Accurate mass spec.: m/z 350.2230 [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. customto give 6.8 mg (quant.) as a colorless film

Sources & evidence

ORD record
ord-54ab3c98fe634f55bc00c091e68005b4
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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