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

HRID 2056706노트

반응식

HRID 2056706 반응식
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

참가 물질

8

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5b401ed6bb2e43ba9516bd885972a2a7
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07335672B2

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