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

HRID 555860노트

반응식

HRID 555860 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-bdf88d72fc414f3f82bbbf76d650d14a
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053438B2

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