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Diisopropylethylamine → Methyl 2-((4-(4-(3-cyclobutylureido)benzoyl)piperazin-1-yl)methyl)oxazole-4-carboxylate

HRID 408846
ノート
印刷プレビュー

反応式

HRID 408846 の反応式
FC(F)(F)C(O)=O.[N:8]1([CH2:14][C:15]2[O:16][CH:17]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[N:19]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[CH:24]1([NH:28][C:29](=[O:40])[NH:30][C:31]2[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=2)[CH2:27][CH2:26][CH2:25]1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH:24]1([NH:28][C:29](=[O:40])[NH:30][C:31]2[CH:32]=[CH:33][C:34]([C:35]([N:11]3[CH2:12][CH2:13][N:8]([CH2:14][C:15]4[O:16][CH:17]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[N:19]=4)[CH2:9][CH2:10]3)=[O:36])=[CH:38][CH:39]=2)[CH2:25][CH2:26][CH2:27]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 81531DiisopropylethylamineHCID 624152074-(3-Cyclobutylureido)benzoic acidHCID 66661413Methyl 2-(piperazin-1-yl-methyl)oxazole-4-carboxylate 2,2,2-trifluoroacetate

生成物 1

HCID 58055798Methyl 2-((4-(4-(3-cyclobutylureido)benzoyl)piperazin-1-yl)methyl)oxazole-4-carboxylate収率 15%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
2 回

実験手順

To a N,N-dimethylformamide (3 mL) solution of methyl 2-(piperazin-1-yl-methyl)oxazole-4-carboxylate 2,2,2-trifluoroacetate (174 mg, 513 μmol) and 4-(3-cyclobutylureido)benzoic acid (120 mg, 513 μmol) in N,N-dimethylformamide (5 mL) was added N,N-diisopropylethylamine (357 μL, 2.05 mmol), followed by O-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyl uronium hexafluorophosphate (293 mg, 770 μmol; HATU). The mixture was stirred at room temperature for 22 hours and was then concentrated under vacuum. The residue was taken up in ethyl acetate and washed with saturated aqueous ammonium chloride and brine. The organic phase was dried on magnesium sulfate, filtered and concentrated under vacuum. The crude residue was applied to a silica gel column and eluted with 25% ethyl acetate in n-hexanes to give the title compound (34 mg). MS (ESI) m/z 442.1 [M+H]+

後処理

  1. concentrationwas then concentrated under vacuum
  2. washwashed with saturated aqueous ammonium chloride and brine
  3. customThe organic phase was dried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. washeluted with 25% ethyl acetate in n-hexanes

出典と根拠

ORDレコード
ord-19183c09759242dc89f96965b528b391
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08759352B2

反応ノート

読み込み中…

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