HCID 57545968, compound → HCID 25159653, compound

HRID 913984Notes

Reaction equation

HRID 913984 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][O:12][CH2:13][C:14]3([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[CH:10]=1)[NH:7][N:6]=[CH:5]2>FC(F)(F)C(O)=O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][O:12][CH2:13][C:14]3([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[CH:10]=1)[NH:7][N:6]=[CH:5]2

Participants

3

Reactant 1

HCID 57545968HCID 57545968, compound

Product 1

HCID 25159653HCID 25159653, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(((5-methyl-1H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (12 mg, 0.028 mmol) was dissolved in trifluoroacetic acid (25% in dichloromethane, 4 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 9.4 mg (quant.) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 9.43 (bs, 1H), 7.85 (s, 1H), 7.47 (m, 2H), 7.39 (m, 4H), 7.25 (s, 1H), 6.89 (s, 1H), 4.65 (s, 2H), 3.56 (s, 2H), 2.91 (m, 2H), 2.77 (m, 2H), 2.38 (s, 3H), 2.21 (m, 2H), 1.99 (bs, 1H), 1.86 (m, 2H); 13C-NMR (CDCl3, 126 MHz) δ 144.2, 137.3, 133.8, 129.9, 128.9, 127.1, 126.8, 126.0, 124.1, 120.5, 119.1, 80.6, 72.4, 42.7, 41.7, 33.9, 21.3. Mass spec.: 336.13 (MH)+. Accurate mass spec.: m/z 336.2066 [MH]+, Δ=2.9 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 9.4 mg (quant.) as a colorless film

Sources & evidence

ORD record
ord-045fa46ed9d5490182363df9a17fc049
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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