Trifluoroacetic acid → Sorafenib related compound 10

HRID 1184943노트

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HRID 1184943 반응식
[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]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57541570HCID 57541570, 화합물

생성물 1

HCID 59772925Sorafenib related compound 10수율 90%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8cf10e22a5214a1e980186e7f998e615
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669369B2

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