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 491845노트

반응식

HRID 491845 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-d7e2f97716194b9a96e57aa9b85b9965
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531560B2

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