Cesium carbonate → N-(4-(3-(4-Fluorotetrahydro-2H-pyran-4-YL)pyrazin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

HRID 887447노트

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HRID 887447 반응식
F[C:2]1[C:7]([C:8]2([F:14])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:5]=[CH:4][N:3]=1.[S:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[NH:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[F:14][C:8]1([C:7]2[C:2]([O:31][C:28]3[CH:27]=[CH:26][C:25]([NH:24][C:16]4[S:15][C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=5[N:17]=4)=[CH:30][CH:29]=3)=[N:3][CH:4]=[CH:5][N:6]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 593268134-(Benzo[d]thiazol-2-ylamino)phenolHCID 593511352-Fluoro-3-(4-fluorotetrahydro-2H-pyran-4-YL)pyrazine

생성물 1

HCID 59351165N-(4-(3-(4-Fluorotetrahydro-2H-pyran-4-YL)pyrazin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
80 °C

실험 절차

To a solution of 2-fluoro-3-(4-fluorotetrahydro-2H-pyran-4-yl)pyrazine (0.055 g, 0.275 mmol) and 4-(benzo[d]thiazol-2-ylamino)phenol (0.100 g, 0.412 mmol) in DMSO (0.9 mL) was added cesium carbonate (0.179 g, 0.549 mmol). The resulting mixture was heated to 80° C. overnight. The reaction mixture was partitioned between water, brine and DCM. The aqueous layer was back extracted with DCM and the combined organic layer was dried (Na2SO4) and concentrated. Purification by prep-plate TLC (5% MeOH/DCM) produced product. MS (ESI, pos. ion) m/z: 423.0 (M+1). IC50 (uM) +++++.

후처리

  1. customThe reaction mixture was partitioned between water, brine and DCM
  2. extractionThe aqueous layer was back extracted with DCM
  3. dry with materialthe combined organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by prep-plate TLC (5% MeOH/DCM)
  6. customproduced product

출처 및 근거

ORD 기록
ord-3a2f986065374eba908b128bcf07408e
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247418B2

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