Potassium Carbonate → N-(4-(2-(1-(4-Fluorophenyl)ethoxy)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

HRID 2056706Notes

Reaction equation

HRID 2056706 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[C:14]3[N:15]=[C:16]([NH:18][C:19](=[O:21])[CH3:20])[S:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[N:3]=1.[F:32][C:33]1[CH:41]=[CH:40][C:36]([CH:37]([OH:39])[CH3:38])=[CH:35][CH:34]=1.C([O-])([O-])=O.[K+].[K+].CS(O[Na])=O>CN(C=O)C.O.CCOC(C)=O>[F:32][C:33]1[CH:41]=[CH:40][C:36]([CH:37]([O:39][C:2]2[N:7]=[C:6]([O:8][C:9]3[C:14]4[N:15]=[C:16]([NH:18][C:19](=[O:21])[CH3:20])[S:17][C:13]=4[CH:12]=[CH:11][CH:10]=3)[CH:5]=[C:4]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)[N:3]=2)[CH3:38])=[CH:35][CH:34]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 739461-(4-Fluorophenyl)ethanolHCID 58612070N-{4-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzo[d]thiazol-2-yl}-acetamideHCID 178504973HCID 178504973, compound

Product 1

HCID 58612042N-(4-(2-(1-(4-Fluorophenyl)ethoxy)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-{4-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzo[d]thiazol-2-yl}-acetamide (465 mg, 1.0 mmol, Example 7(d)), 4-fluoro-α-methylbenzyl-alcohol (140 mg, 1 mmol, Aldrich), K2CO3 (207 mg, 1.5 mmol) and 85% MeSO2Na (30 mg, 0.25 mmol, Aldrich) in DMF (50 mL) was heated at 120° C. with stirring for 5 h. The reaction mixture was allowed to reach room temperature and was diluted with water (50 mL), and exacted with EtOAc (2×50 mL). The organic phase was washed with brine (10 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue purified by silica gel column chromatography (20% EtOAc/hexane) to give the title compound. MS (ESI, pos. ion) m/z: 569 (M+1).

Workup

  1. customto reach room temperature
  2. washThe organic phase was washed with brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue purified by silica gel column chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-5b401ed6bb2e43ba9516bd885972a2a7
Source dataset
uspto-grants-2008_02
Patent number
US07335672B2

Reaction notes

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