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

HRID 491845ノート

反応式

HRID 491845 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]=[CH:42][C:41]=1[O:50][CH3:51].C([O-])(O)=O.[Na+]>C1COCC1>[C:46]([C:44]1[CH:43]=[CH:42][C:41]([O:50][CH3:51])=[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

6

反応物 4

HCID 516892Sodium BicarbonateHCID 2733832Lithium HexamethyldisilazideHCID 15724682Methyl 5-(tert-butyl)-2-methoxybenzoateHCID 576788803-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-phenylamine

生成物 1

HCID 116637735-tert-butyl-N-{3-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-phenyl}-2-methoxy-benzamide収率 50.5%

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 51.8 mg (0.23 mmol) of 5-tert-butyl-2-methoxy-benzoic acid methyl ester in 5 mL of THF was added. The mixture was stirred at 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 (62 mg, 50%). ESI MS m/z 534 [C33H35N5O2+H]+.

後処理

  1. stirringThe mixture was stirred at 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-d7e2f97716194b9a96e57aa9b85b9965
出典データセット
uspto-grants-2009_05
特許番号
US07531560B2

反応ノート

読み込み中…