HCID 57545979, compound → HCID 25159918, compound

HRID 913998Notes

Reaction equation

HRID 913998 reaction equation
[C:1]1([C:7]2([CH2:20][O:21][CH:22]([C:24]3[C:32]4[C:28](=[CH:29][N:30](COCC[Si](C)(C)C)[N:31]=4)[CH:27]=[C:26]([C:41]([F:44])([F:43])[F:42])[CH:25]=3)[CH3:23])[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>FC(F)(F)C(O)=O>[C:1]1([C:7]2([CH2:20][O:21][CH:22]([C:24]3[CH:25]=[C:26]([C:41]([F:42])([F:44])[F:43])[CH:27]=[C:28]4[C:32]=3[NH:31][N:30]=[CH:29]4)[CH3:23])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 57545979HCID 57545979, compound

Product 1

HCID 25159918HCID 25159918, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(±)-tert-Butyl 4-phenyl-4-((1-(5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethoxy)methyl)piperidine-1-carboxylate (62 mg, 0.098 mmol) was dissolved in trifluoroacetic acid (50% in dichloromethane, 1.5 mL) and stirred at room temperature for 3 h. 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 41 mg (quant.). 1H-NMR (CDCl3, 500 MHz) δ 10.03 (bs, 1H), 8.08 (m, 1H), 7.95 (m, 1H), 7.32-7.55 (m, 5H), 7.26 (m, 1H), 4.66 (m, 1H), 3.54 (m, 2H), 3.36 (m, 2H), 2.72-3.06 (m, 4H), 2.36 (m, 1H), 2.16 (m, 1H), 1.97 (m, 1H), 1.85 (m, 1H), 1.49 (m, 3H); 13C-NMR (CDCl3, 126 MHz) δ 143.8, 138.1, 135.2, 128.8, 127.5, 127.1, 126.8, 124.7 (q, J=272 Hz), 123.3, 119.7 (q, J=3.8 Hz), 118.1 (q, J=3.8 Hz), 79.2, 78.3, 42.8, 42.6, 41.7, 33.8, 33.7, 22.2. Mass spec.: 404.19 (MH)+. Accurate mass spec.: m/z 404.1960 [MH]+, Δ=2.5 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 41 mg (quant.)

Sources & evidence

ORD record
ord-8931802fe95a4ec59adb6f9fadc05d80
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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