Imidazole → [5-(2-Imidazol-1-yl-pyridin-4-yl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine

HRID 1951177ノート

反応式

HRID 1951177 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([NH:13][C:14]3[CH:19]=[N:18][CH:17]=[CH:16][N:15]=3)=[N:10][C:9]=2[CH3:20])[CH:5]=[CH:4][N:3]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[N:21]1([C:2]2[CH:7]=[C:6]([C:8]3[S:12][C:11]([NH:13][C:14]4[CH:19]=[N:18][CH:17]=[CH:16][N:15]=4)=[N:10][C:9]=3[CH3:20])[CH:5]=[CH:4][N:3]=2)[CH:25]=[CH:24][N:23]=[CH:22]1

参加物

6

反応物 3

HCID 795ImidazoleHCID 10796Cesium carbonateHCID 11301149[5-(2-Chloro-pyridin-4-yl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine

生成物 1

HCID 11232938[5-(2-Imidazol-1-yl-pyridin-4-yl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

A stirred solution of [5-(2-Chloro-pyridin-4-yl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine (Ex. 2b, 0.4 g, 1.32 mmol) in DMSO (10 ml) is treated with imidazole (0.18 g, 2.64 mmol) followed by caesium carbonate (0.86 g, 2.64 mmol). The reaction mixture is heated to 140° C. for 48 hours and then allowed to cool to room temperature. The mixture is diluted with water (100 ml) and extracted with ethyl acetate (4×100 ml). The organics are combined, dried over MgSO4 and the solvent removed in vacuo to yield the crude product as a yellow oil. Purification by chromatography on silica, eluting with ethyl acetate-methanol (9:1) affords the titled compound.

後処理

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate (4×100 ml)
  3. dry with materialdried over MgSO4
  4. customthe solvent removed in vacuo
  5. customto yield the crude product as a yellow oil
  6. customPurification by chromatography on silica
  7. washeluting with ethyl acetate-methanol (9:1)

出典と根拠

ORDレコード
ord-836e663510a7495d90d78c935f503d1f
出典データセット
uspto-grants-2013_03
特許番号
US08404684B2

反応ノート

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