HCID 87858867, compound → HCID 10107679, compound

HRID 1765998Notes

Reaction equation

HRID 1765998 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[C:16]([Cl:24])[N:15]=2)[CH2:10][C@@H:9]1[CH3:25])=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:24][C:16]1[N:15]=[C:14]([N:11]2[CH2:12][CH2:13][NH:8][C@@H:9]([CH3:25])[CH2:10]2)[CH:19]=[CH:18][C:17]=1[C:20]([F:23])([F:21])[F:22]

Participants

3

Reactant 1

HCID 87858867HCID 87858867, compound

Product 1

HCID 10107679HCID 10107679, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 4-(6-chloro-5-trifluoromethyl-pyridin-2-yl)-2-(S)-methyl-piperazine-1-carboxylic acid tert-butyl ester (7.80 g, 26.4 mmol) was dissolved in CH2Cl2/TFA (50:50; 30 mL) and stirred at room temperature over night. The solvent was removed at reduced pressure and the resulting oil was taken up between alkaline water (NaOH) and CHCl3. The aqueous phase was extracted once with CHCl3, the combined organic phases were dried (MgSO4) and the solvent was evaporated at reduced pressure to yield 5.79 g (78%) of a light yellow oil. A NOE between the methylene protons at C-2 in the piperazine ring and the C3-hydrogen in the pyridine ring was observed. Purity 100% (HPLC). Fragmenting MS analysis supports the stated structure. HRMS m/z calcd for C11H13ClF3N3 (M)+ 279.0750. found 279.0751

Workup

  1. customThe solvent was removed at reduced pressure
  2. extractionThe aqueous phase was extracted once with CHCl3
  3. dry with materialthe combined organic phases were dried (MgSO4)
  4. customthe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-c32b6d88832d49668bd41ef90af330b8
Source dataset
uspto-grants-2007_06
Patent number
US07229997B2

Reaction notes

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