Ethyl Acetate → 2-Chloro-4-[4-(2-methoxy-ethoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile

HRID 2233594Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[C:31]#[N:32])[O:5][CH2:6][C:7]1[S:11][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:9][C:8]=1[CH2:22][O:23]S(C)(=O)=O.[H-].[Na+].[C:35]([O:38][CH2:39]C)(=O)[CH3:36]>COCCO>[Cl:1][C:2]1[CH:3]=[C:4]([O:5][CH2:6][C:7]2[S:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=3)=[N:9][C:8]=2[CH2:22][O:23][CH2:36][CH2:35][O:38][CH3:39])[CH:28]=[CH:29][C:30]=1[C:31]#[N:32]

Participants

Conditions

Temperature: 50 °C

Procedure

120 mg Methanesulfonic acid 5-(3-chloro-4-cyano-phenoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethyl ester were dissolved in 5 ml 2-methoxyethanol. 10.0 mg sodium hydride were added and the mixture stirred at 50° C. for one hour. The reaction mixture was diluted by addition of 50 ml ethyl acetate, washed with brine then dried over MgSO4. The solvent was removed in vacuo and the residue purified by RP-HPLC to provide 30 mg of 2-Chloro-4-[4-(2-methoxy-ethoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile as lyophilisate.

Workup

washwashed with brine
dry with materialthen dried over MgSO4
customThe solvent was removed in vacuo
customthe residue purified by RP-HPLC

Sources & evidence

ORD record: ord-34be27bcb09b44068558526d464502d5
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709509B2

Reaction notes

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