Cesium carbonate → 3-Fluoro-4-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}-N-(1,3-thiazol-2-yl)benzenesulfonamide

HRID 337734노트

반응식

HRID 337734 반응식
[F:1][C:2]1[CH:3]=[C:4]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:5]=[CH:6][C:7]=1[O:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@@H:10]1[C:14]1[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=1.Br[C:25]1[S:26][CH:27]=[CH:28][N:29]=1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Cu](I)I>[F:1][C:2]1[CH:3]=[C:4]([S:20]([NH:23][C:25]2[S:26][CH:27]=[CH:28][N:29]=2)(=[O:21])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@@H:10]1[C:14]1[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 764302-BromothiazoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 899632593-Fluoro-4-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}benzenesulfonamide

생성물 1

HCID 899636633-Fluoro-4-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}-N-(1,3-thiazol-2-yl)benzenesulfonamide수율 86%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매

실험 절차

A solution of the 3-fluoro-4-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}benzenesulfonamide (0.07 g, 0.21 mmol) prepared in Example 16c, 2-bromothiazole (0.07 g, 0.41 mmol), copper iodide (0.01 g, 0.04 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (0.01 g, 0.09 mmol) and cesium carbonate (0.20 g, 0.62 mmol) in DMF (2.0 mL) was stirred at 120° C. for 20 hours under the nitrogen atmosphere. After allowing to cool, the reaction solution was vacuum concentrated, and the residue was purified with HPLC to yield the title compound (75 mg, 86%) as a colorless solid.

후처리

  1. temperatureto cool
  2. concentrationconcentrated
  3. customthe residue was purified with HPLC

출처 및 근거

ORD 기록
ord-aece0d123fa14c5fa4b22a9eede1b510
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889741B2

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