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Sodium Bicarbonate → 5-tert-butyl-N-{3-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-phenyl}-3-methanesulfonylamino-2-methoxy-benzamide

HRID 491844
ノート
印刷プレビュー

反応式

HRID 491844 の反応式
[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[CH:5][C:4]=1[C:14]1[N:15]=[CH:16][N:17]([C:19]2[CH:20]=[C:21]([NH2:26])[CH:22]=[CH:23][C:24]=2[CH3:25])[CH:18]=1)[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C[O:38][C:39](=O)[C:40]1[CH:45]=[C:44]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH:43]=[C:42]([NH:50][S:51]([CH3:54])(=[O:53])=[O:52])[C:41]=1[O:55][CH3:56].C([O-])(O)=O.[Na+]>C1COCC1>[C:46]([C:44]1[CH:43]=[C:42]([NH:50][S:51]([CH3:54])(=[O:53])=[O:52])[C:41]([O:55][CH3:56])=[C:40]([CH:45]=1)[C:39]([NH:26][C:21]1[CH:22]=[CH:23][C:24]([CH3:25])=[C:19]([N:17]2[CH:18]=[C:14]([C:4]3[CH:5]=[N:6][N:7]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:3]=3[CH2:1][CH3:2])[N:15]=[CH:16]2)[CH:20]=1)=[O:38])([CH3:49])([CH3:47])[CH3:48]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 2733832Lithium hexamethyldisilazaneHCID 576788635-Tert-butyl-3-methanesulfonylamino-2-methoxy-benzoic acid methyl esterHCID 576788803-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-phenylamine

生成物 1

HCID 117001245-tert-butyl-N-{3-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-phenyl}-3-methanesulfonylamino-2-methoxy-benzamide
収率 40.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

3-[4-(5-Ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-phenylamine (Example 3) (80 mg, 0.23 mmol) was dissolved in THF (5 mL) under N2 and 0.9 mL of 1 M LiHMDS (0.9 mmol) was slowly added. After stirring for 5 min, a solution of 73.5 mg (0.23 mmol) of 5-tert-butyl-3-methanesulfonylamino-2-methoxy-benzoic acid methyl ester (Example 1) in 5 mL of THF was added. The mixture was stirred at room temperature for 45 min, then saturated NaHCO3 (10 mL) was slowly added. The resulting mixture was then extracted with CH2Cl2 (100 mL). Chromatography (30 to 100% EtOAc in hexanes) provided the title compound as a tan foam (58 mg, 40%). ESI MS m/z 627 [C34H38N6O4S+H]+.

後処理

  1. stirringThe mixture was stirred at room temperature for 45 min
  2. extractionThe resulting mixture was then extracted with CH2Cl2 (100 mL)

出典と根拠

ORDレコード
ord-9dfeb1ef5800428494cb680e8a31a91a
出典データセット
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07531560B2

反応ノート

読み込み中…

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