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

HRID 887447ノート

反応式

HRID 887447 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

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) +++++.

後処理

  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

出典と根拠

ORDレコード
ord-3a2f986065374eba908b128bcf07408e
出典データセット
uspto-grants-2012_08
特許番号
US08247418B2

反応ノート

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