Ammonia → 3-Chloro-4-(4-phenylpyrimidin-2-ylamino)benzamide

HRID 1473856ノート

反応式

HRID 1473856 の反応式
C[Al](C)C.[NH3:5].O1CCOCC1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[NH:22][C:23]1[N:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:25][N:24]=1)[C:16]([O-])=[O:17]>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[NH:22][C:23]1[N:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:25][N:24]=1)[C:16]([NH2:5])=[O:17]

参加物

6

反応物 4

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 16682925TrimethylaluminumHCID 866478723-Chloro-4-(4-phenylpyrimidin-2-ylamino)benzoate

生成物 1

HCID 595881623-Chloro-4-(4-phenylpyrimidin-2-ylamino)benzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trimethylaluminum (0.8 mL, 2.0 mmol, 2.5M in hexanes) was slowly added to a solution of ammonia in dioxane (4 mL, 0.5 mmol) under argon at room temperature. After stirring for 15 min at room temperature, 3-chloro-4-(4-phenylpyrimidin-2-ylamino)benzoate (0.67 g, 2.0 mmol) in CH2Cl2 was added slowly. The mixture was stirred at room temperature until the ester had been consumed as judged by analytical HPLC analysis. The reaction was quenched with 1 N HCl and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×), and the combined organics were dried (MgSO4) and concentrated to afford (3-chloro-4-(4 phenylpyrimidin-2-ylamino)benzamide. MS (ESI) 325 (M+H).

後処理

  1. customhad been consumed
  2. customThe reaction was quenched with 1 N HCl
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  5. dry with materialthe combined organics were dried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-1f70c260b8ee460ca0d190868f5d6053
出典データセット
uspto-grants-2015_04
特許番号
US09018205B2

反応ノート

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