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Hexamethyldisilazane → {3-[(5-biphenyl-4-yl-6-fluoro-1H-benzimidazol-2-yl)oxy]phenyl}phosphonic acid

HRID 1960137
ノート
印刷プレビュー

反応式

HRID 1960137 の反応式
C([O:4][P:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[NH:22][C:21]3[CH:23]=[C:24]([F:39])[C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[CH:29][CH:28]=4)=[CH:26][C:20]=3[N:19]=2)[CH:12]=1)(=[O:10])[O:6]C(C)C)(C)C.C[Si](N[Si](C)(C)C)(C)C.Br[Si](C)(C)C>C(Cl)Cl>[C:30]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:29]=[CH:28][C:27]([C:25]2[C:24]([F:39])=[CH:23][C:21]3[NH:22][C:18]([O:17][C:13]4[CH:12]=[C:11]([P:5](=[O:4])([OH:10])[OH:6])[CH:16]=[CH:15][CH:14]=4)=[N:19][C:20]=3[CH:26]=2)=[CH:32][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 13838HexamethyldisilazaneHCID 76113BromotrimethylsilaneHCID 86658719[3-(5-biphenyl-4-yl-6-fluoro-1H-benzoimidazol-2-yloxy)-phenyl]-phosphonic acid diisopropyl ester

生成物 1

HCID 58482531{3-[(5-biphenyl-4-yl-6-fluoro-1H-benzimidazol-2-yl)oxy]phenyl}phosphonic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of compound 13-8 (40 mg, 0.073 mmol) in 3 mL of CH2Cl2 was added hexamethyldisilizane (0.3 mL), followed by bromo trimethylsilane (0.1 mL, 0.74 mmol). The reaction was allowed to stir for 18 h at ambient temperature. The organic solvent was removed in vacuo, followed by the addition of H2O (1 mL). The crude product was sonicated and yielded a white suspension. Solvent was removed in vacuo and the product was dissolved in DMSO (1.5 mL). The product was purified by prepatory HPLC using a 30-80% CH3CN with 0.05% trifluoroacetic acid gradient over 20 minutes. The pure fractions were combined and lyophilized to give the desired title compound 13-9. 1H NMR δ 7.35-7.41 (2H, m), 7.48-7.51 (3H, m), 7.56-7.66 (6H, m), 7.72-7.77 (4H, m); LC-MS: m/e 461(M+H)+.

後処理

  1. customThe organic solvent was removed in vacuo
  2. additionfollowed by the addition of H2O (1 mL)
  3. customThe crude product was sonicated
  4. customyielded a white suspension
  5. customSolvent was removed in vacuo
  6. dissolutionthe product was dissolved in DMSO (1.5 mL)
  7. customThe product was purified by prepatory HPLC
  8. waitgradient over 20 minutes

出典と根拠

ORDレコード
ord-9b9bb6e2735f4bbf969342d3fd027a62
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08410284B2

反応ノート

読み込み中…

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