Water → 2-Chloro-4-[4-(2-morpholin-4-yl-ethoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile

HRID 2263424Notes

Reaction equation

HRID 2263424 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+].O.O[CH2:37][CH2:38][N:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>>[Cl:1][C:2]1[CH:3]=[C:4]([O:5][CH2:6][C:7]2[S:11][C:10]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:16][CH:17]=3)=[N:9][C:8]=2[CH2:22][O:23][CH2:37][CH2:38][N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)[CH:28]=[CH:29][C:30]=1[C:31]#[N:32]

Participants

5

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 611632-MorpholinoethanolHCID 59296164Methanesulfonic acid 5-(3-chloro-4-cyano-phenoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethyl ester

Product 1

HCID 595948242-Chloro-4-[4-(2-morpholin-4-yl-ethoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile

Conditions

Temperature
50 °C

Procedure

120 mg Methanesulfonic acid 5-(3-chloro-4-cyano-phenoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethyl ester was dissolved in 5 ml N-(2-hydroxyethyl)morpholine. 10 mg sodium hydride were added and the reaction mixture stirred at 50° C. for one hour. 10 ml water was added and the reaction mixture extracted 50 ml ethyl acetate. The organic layer was separated and washed twice with 20 ml brine. The organic layer was dried over MgSO4 and the solvent was then removed in vacuo. The residue was purified by RP-HPLC to obtain 40 mg 2-chloro-4-[4-(2-morpholin-4-yl-ethoxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile as its trifluoro-acetate salt.

Workup

  1. extractionthe reaction mixture extracted 50 ml ethyl acetate
  2. customThe organic layer was separated
  3. washwashed twice with 20 ml brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was then removed in vacuo
  6. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-5812b0b1fc5c42a991e3192c893027d6
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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