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Thiazole → 2-Chloro-4-[4-(tetrahydro-pyran-2-yloxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile

HRID 2233590
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HRID 2233590 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[CH2:18][O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1.S1C=CN=C1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:37][C:38]1[CH:45]=[C:44]([OH:46])[CH:43]=[CH:42][C:39]=1[C:40]#[N:41]>CN(C)C=O.C(OC(=O)C)C>[Cl:37][C:38]1[CH:45]=[C:44]([O:46][CH2:2][C:3]2[S:7][C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:17])[F:15])=[CH:10][CH:9]=3)=[N:5][C:4]=2[CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH:43]=[CH:42][C:39]=1[C:40]#[N:41]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 9256ThiazoleHCID 10796Cesium carbonateHCID 5927972-Chloro-4-hydroxybenzonitrileHCID 211094595-(chloromethyl)-4-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole

생성물 1

HCID 592961302-Chloro-4-[4-(tetrahydro-pyran-2-yloxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile수율 105.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

3.0 g 5-(Chloromethyl)-4-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2-[4-(trifluormethyl)phenyl]-1,3-thiazole (synthesis is described in WO2002/067912) thiazole were dissolved in 100 ml dimethylformamide. 5.0 g of cesium carbonate and 1.53 g 2-Chloro-4-hydroxybenzonitrile were added and the mixture was stirred at room temperature overnight. Then 300 ml of ethylacetate were added, the mixture washed three times with saturated NaHCO3 solution and brine then dried over MgSO4. The solvent was removed in vacuo to obtain 4.1 g of crude 2-Chloro-4-[4-(tetrahydro-pyran-2-yloxymethyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzonitrile as yellow oil. This material was used without further purification.

후처리

  1. washthe mixture washed three times with saturated NaHCO3 solution and brine
  2. dry with materialthen dried over MgSO4
  3. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-3500fc2fa63d4dfa9978e28ac6cdb6d1
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07709509B2

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