Ethyl Acetate → HCID 59295479, compound

HRID 2233306Notes

Reaction equation

HRID 2233306 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[S:16][C:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:14][C:13]=2[CH3:23])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(N(CC)C(C)C)(C)C.[F:33][C:34]([F:45])([F:44])[CH2:35]OS(C(F)(F)F)(=O)=O.C(OCC)(=O)C>O1CCCC1>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[S:16][C:15]([CH:17]3[CH2:22][CH2:21][N:20]([CH2:35][C:34]([F:45])([F:44])[F:33])[CH2:19][CH2:18]3)=[N:14][C:13]=2[CH3:23])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 81531DiisopropylethylamineHCID 59295393HCID 59295393, compound

Product 1

HCID 59295479HCID 59295479, compoundYield 114%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

710 mg 2-Chloro-4-(4-methyl-2-piperidin-4-yl-thiazol-5-ylmethoxy)-benzonitrile were dissolved in 20 ml tetrahydrofuran. 0.55 ml N,N-Diisopropylethylamine and 710 mg 2,2,2-Trifluoroethyl-trifluoromethanesulfonate were added and the reaction mixture heated under reflux for two hours. The cooled reaction mixture was diluted by addition of 100 ml ethyl acetate, washed with 20 ml water and brine then dried over MgSO4. The solvent was removed in vacuo to obtain 1.0 g crude 2-Chloro-4-{4-methyl-2-[1-(2,2,2-trifluoro-ethyl)-piperidin-4-yl]-thiazol-5-ylmethoxy}-benzonitrile.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for two hours
  3. customThe cooled reaction mixture
  4. washwashed with 20 ml water and brine
  5. dry with materialthen dried over MgSO4
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6b35b40972d7486eb4df0974f35b7d01
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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