HCID 86626242, compound → HCID 67403196, compound

HRID 913864Notes

Reaction equation

HRID 913864 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:21][O:22][CH2:23][C:24]3[CH:25]=[C:26]([O:33][CH3:34])[CH:27]=[C:28]4[C:32]=3[NH:31][N:30]=[CH:29]4)[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:21][O:22][CH2:23][C:24]3[CH:25]=[C:26]([O:33][CH3:34])[CH:27]=[C:28]4[C:32]=3[NH:31][N:30]=[CH:29]4)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86626242HCID 86626242, compound

Product 1

HCID 67403196HCID 67403196, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(±)-tert-Butyl 4-(4-fluorophenyl)-4-((1-(5-methoxy-1H-indazol-7-yl)methoxy)methyl)piperidine-1-carboxylate (20 mg, 0.041 mmol) was dissolved in trifluoroacetic acid (20% in dichloromethane, 1.5 mL) and stirred at room temperature for 30 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 15 mg (95%). LC/MS (HPLC method 3): tR=2.387 min, 384.41(MH)+.

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 15 mg (95%)

Sources & evidence

ORD record
ord-65cf71a5c7044be2adf09c26c2643a0c
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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