Tributylamine → HCID 178517386, compound

HRID 1786305Notes

Reaction equation

HRID 1786305 reaction equation
[CH:1]1([C:8](=O)[CH:9]([C:15]2[C:20]([F:21])=[CH:19][C:18]([F:22])=[CH:17][C:16]=2[F:23])[C:10](OCC)=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:25][C:26]1[N:30]=[CH:29][NH:28][N:27]=1.C(N(CCCC)CCCC)CCC>C(OCC)(=O)C>[CH:1]1([C:8]2[N:27]3[N:28]=[CH:29][N:30]=[C:26]3[N:25]=[C:10]([OH:11])[C:9]=2[C:15]2[C:20]([F:21])=[CH:19][C:18]([F:22])=[CH:17][C:16]=2[F:23])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7622TributylamineHCID 67047753HCID 67047753, compoundHCID 178418311HCID 178418311, compound

Product 1

HCID 178517386HCID 178517386, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of ethyl 3-cycloheptyl-3-oxo-2-(2,4,6-trifluorophenyl)propanoate (342 mg, 1.0 mmol), 3-amino-1,2,4-triazole (84 mg, 1.0 mmol), and tributylamine (185 mg, 1.0 mmol) is stirred under nitrogen atmosphere at 160° C. for 2.5 h and cooled to room temperature. The mixture is dissolved in ethyl acetate and the organic layer is washed with 1.0 N hydrochloric acid and saturated sodium chloride, dried over magnesium sulfate, and concentrated to a solid. The solid thus obtained is washed with hexanes to give crude 7-cycloheptyl-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-5-ol as a light tan solid (225 mg). MS: m/z 363.2 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. washthe organic layer is washed with 1.0 N hydrochloric acid and saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to a solid
  5. customThe solid thus obtained
  6. washis washed with hexanes

Sources & evidence

ORD record
ord-5bec2205b16f45e0a6de23685051a431
Source dataset
uspto-grants-2009_03
Patent number
US07507739B2

Reaction notes

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