Water → HCID 67265611、化合物

HRID 1425509ノート

反応式

HRID 1425509 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:12]=[N:11][N:10]([CH3:13])[C:9]=1[C:14]1[CH:15]=[C:16]([NH:21][C:22](=[O:33])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[CH:17]=[CH:18][C:19]=1[OH:20].CS(O[CH2:39][C:40]([CH3:45])([N+:42]([O-:44])=[O:43])[CH3:41])(=O)=O.O>CC(N(C)C)=O>[N+:42]([C:40]([CH3:45])([CH3:41])[CH2:39][O:20][C:19]1[CH:18]=[CH:17][C:16]([NH:21][C:22](=[O:33])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:31])([F:30])[F:32])[CH:24]=2)=[CH:15][C:14]=1[C:9]1[N:10]([CH3:13])[N:11]=[CH:12][C:8]=1[Cl:7])([O-:44])=[O:43]

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 204526582-Methyl-2-nitropropyl methanesulfonateHCID 136387987HCID 136387987、化合物

生成物 1

HCID 67265611HCID 67265611、化合物収率 68%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
160 °C

実験手順

Cesium carbonate (815 mg, 2.50 mmol) was added to a solution of N-(3-(4-chloro-2-methyl-2H-pyrazol-3-yl)-4-hydroxyphenyl)-3-(trifluoromethyl)benzamide (396 mg, 1.00 mmol) and 2-methyl-2-nitropropyl methanesulfonate (276 mg, 1.40 mmol) in DMA (2.0 mL), and the mixture was stirred at 160° C. After 1 hour, the mixture was allowed to cool to room temperature and poured into water, and the resulting suspension was extracted with dichloromethane. The extract was dried with sodium sulfate, filtered, and evaporated to dryness. The crude product was purified by flash chromatography (ethyl acetate hexanes 1:2) to afford the title compound (338 mg, 68%) as a yellow oil. LCMS m/z (%)=499.5 (M+H, 37Cl 31.5), 497.4 (M+H, 35Cl 100.0). 1H NMR (400 MHz, CDCl3) δ 1.51 (s, 3H) 1.57 (s, 3H) 3.64 (s, 3H) 4.01 (d, J=9.85 Hz, 1H) 4.49 (d, J=9.85 Hz, 1H) 7.08 (d, J=8.84 Hz, 1H) 7.49 (d, J=2.53 Hz, 1H) 7.51 (s, 1H) 7.65 (t, J=7.71 Hz, 1H) 7.79-7.89 (m, 3H) 8.07 (d, J=7.83 Hz. 1H) 8.13 (s, 1H).

後処理

  1. temperatureto cool to room temperature
  2. extractionthe resulting suspension was extracted with dichloromethane
  3. dry with materialThe extract was dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by flash chromatography (ethyl acetate hexanes 1:2)

出典と根拠

ORDレコード
ord-ec29cb54fc054be4a499691290fd6129
出典データセット
uspto-grants-2015_01
特許番号
USRE045337E1

反応ノート

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