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Cesium carbonate → 3-(2-(4-(Benzo[D]thiazol-2-ylamino)phenoxy)pyridin-3-YL)cyclopentanol

HRID 410304
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인쇄 미리보기

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HRID 410304 반응식
F[C:2]1[C:7]([CH:8]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[NH:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O.CCOC(C)=O>[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:2]2[C:7]([CH:8]3[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]3)=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:26][CH:25]=1
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 593268134-(Benzo[d]thiazol-2-ylamino)phenolHCID 593271863-(2-Fluoropyridin-3-YL)cyclopentanol

생성물 1

HCID 462148743-(2-(4-(Benzo[D]thiazol-2-ylamino)phenoxy)pyridin-3-YL)cyclopentanol

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매
HCID 13387
N-methyl-2-pyrrolidone
용매

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온도
130 °C

실험 절차

A suspension of 3-(2-fluoropyridin-3-yl)cyclopentanol (869 mg, 4.80 mmol), 4-(benzo[d]thiazol-2-ylamino)phenol (2324 mg, 9.59 mmol) and cesium carbonate (3281 mg, 10.07 mmol) in N-methyl-2-pyrrolidinone (8 mL) was heated to 130° C. under nitrogen. After 9 h, the reaction was cooled to 23° C., diluted with EtOAc (500 mL) and washed with 1N NaOH solution (6×150 mL) and brine (150 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluant: 1-4% methanol/dichloromethane), affording the product as a tan solid. MS (ESI, pos. ion) m/z: 404.1 (M+1). IC50 (uM) +++++.

후처리

  1. temperaturethe reaction was cooled to 23° C.
  2. washwashed with 1N NaOH solution (6×150 mL) and brine (150 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography (eluant: 1-4% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-a7b9212c87944aa0be1267b9143044b0
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08759532B2

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