Trifluoroacetic acid → Sorafenib related compound 10

HRID 1184943ノート

反応式

HRID 1184943 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[NH:10][C:11]2[CH:30]=[CH:29][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([O:24]C(C)(C)C)=[O:23])[CH:17]=3)=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:32]([F:35])([F:34])[F:33].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[NH:10][C:11]2[CH:30]=[CH:29][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([OH:24])=[O:23])[CH:17]=3)=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:32]([F:35])([F:33])[F:34]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57541570HCID 57541570、化合物

生成物 1

HCID 59772925Sorafenib related compound 10収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

At room temperature, tert-butyl 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl) ureido)phenoxy)picolinate (1.4 g, 2.76 mmol) was dissolved in dichloromethane (20 mL). To the resulted solution, trifluoroacetic acid (20 mL) and triethylsilane (0.5 mL) were added. The resulted mixture was heated to 50° C. and stirred for 16 hours. The solvent was removed under reduced pressure, and water (50 mL) and ethyl acetate (70 mL) were added. The resulted mixture was separsted and the organic phase was removed. The aqueous layer was filtered and the solid was washed with water (30 mL×2). The solid was dried under vacumn to give the title compound (1.1 g, purity 97%, yield 90%) as a light green solid.

後処理

  1. customThe solvent was removed under reduced pressure, and water (50 mL) and ethyl acetate (70 mL)
  2. additionwere added
  3. customthe organic phase was removed
  4. filtrationThe aqueous layer was filtered
  5. washthe solid was washed with water (30 mL×2)
  6. customThe solid was dried under vacumn

出典と根拠

ORDレコード
ord-8cf10e22a5214a1e980186e7f998e615
出典データセット
uspto-grants-2014_03
特許番号
US08669369B2

反応ノート

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