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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
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HRID 491844 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]=[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 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

생성물 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
수율 40.2%

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 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]+.

후처리

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

출처 및 근거

ORD 기록
ord-9dfeb1ef5800428494cb680e8a31a91a
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07531560B2

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