HCID 178451995, compound → HCID 178506218, compound

HRID 391464Notes

Reaction equation

HRID 391464 reaction equation
[NH:1]1[C:5]([C:6]2[CH:7]=[C:8]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=2)[CH2:9][O:10][CH2:11][C:12]2([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)=[N:4][N:3]=[N:2]1>FC(F)(F)C(O)=O.C(Cl)Cl>[NH:4]1[C:5]([C:6]2[CH:7]=[C:8]([CH:31]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:33]=2)[CH2:9][O:10][CH2:11][C:12]2([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)=[N:1][N:2]=[N:3]1

Participants

3

Reactant 1

HCID 178451995HCID 178451995, compound

Product 1

HCID 178506218HCID 178506218, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-Butyl 4-((3-(1H-tetrazol-5-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (30.0 mg, 0.058 mmol) was dissolved in a trifluoroacetic acid/methylene chloride mixture (1:1, 1 mL) and stirred under nitrogen for 1 h. The solvent was removed in vacuo and the resulting crude mixture passed through a strong cation exchange column. After washing the column with several volumes of methanol, the product was eluted by washing the column with 2 M ammonia in methanol. Concentration afforded 11.0 mg (45%). LC/MS (HPLC method 3): tR=1.89 min, 418.88 (MH)+.

Workup

  1. customThe solvent was removed in vacuo
  2. washAfter washing the column with several volumes of methanol
  3. washthe product was eluted
  4. washby washing the column with 2 M ammonia in methanol
  5. concentrationConcentration
  6. customafforded 11.0 mg (45%)

Sources & evidence

ORD record
ord-0fcd8a0c112e46df9a1bfd7efce67359
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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