Cesium carbonate → {6-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzo[b]thiophen-3-yl}-acetic acid

HRID 490766노트

반응식

HRID 490766 반응식
Cl[CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH:18]([CH3:20])[CH3:19].C([O:23][C:24](=[O:36])[CH2:25][C:26]1[C:27]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:28]=2[S:29][CH:30]=1)C.C([O-])([O-])=O.[Cs+].[Cs+].[OH-].[Na+]>C(#N)C.C(O)C>[CH:18]([C:4]1[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[S:7][C:3]=1[CH2:2][O:35][C:32]1[CH:33]=[CH:34][C:27]2[C:26]([CH2:25][C:24]([OH:36])=[O:23])=[CH:30][S:29][C:28]=2[CH:31]=1)([CH3:20])[CH3:19]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 57431998(6-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl esterHCID 589340885-Chloromethyl-4-isopropyl-2-[4-(trifluoromethyl)phenyl]thiazole

생성물 1

HCID 10368353{6-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzo[b]thiophen-3-yl}-acetic acid

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6342Acetonitrile용매

실험 절차

To a solution of 5-chloromethyl-4-isopropyl-2-(4-trifluoromethyl-phenyl)-thiazole (100 mg, 0.31 mmol) and (6-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester (75 mg, 0.31 mmol) in acetonitrile (3 mL) is added Cs2CO3 (200 mg, 0.62 mmol). The mixture is stirred at room temperature overnight, ethanol (1 mL) is added, followed by NaOH (5 N, 1.0 mL). The mixture is heated at 50° C. for 2 hrs, solvent is evaporate, the residue is diluted with water, acidified by 5N HCl and extracted with ethyl acetate. Concentration and reversed phase HPLC purification yields the title product. MS (ES): 490.0 (M+−1).

후처리

  1. temperatureThe mixture is heated at 50° C. for 2 hrs
  2. customsolvent is evaporate
  3. additionthe residue is diluted with water
  4. extractionextracted with ethyl acetate
  5. concentrationConcentration
  6. customphase HPLC purification

출처 및 근거

ORD 기록
ord-693ccb0ba6414c359f00c99c86af5c81
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528160B2

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