Hydrochloric Acid → HCID 178428619, 화합물

HRID 2116796노트

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HRID 2116796 반응식
[CH3:1][N:2]1[C:6]([NH:7][C:8](=[O:26])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15][C:16]2[CH:24]=[C:23]3[C:19]([CH2:20][C:21](=[O:25])[NH:22]3)=[CH:18][CH:17]=2)=[CH:5][C:4]([CH3:27])=[N:3]1.[CH:28](OCC)=[O:29].[O-]CC.[Na+].Cl>C(O)C.CCOC(C)=O>[CH3:1][N:2]1[C:6]([NH:7][C:8](=[O:26])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15][C:16]2[CH:24]=[C:23]3[C:19](/[C:20](=[CH:28]/[OH:29])/[C:21](=[O:25])[NH:22]3)=[CH:18][CH:17]=2)=[CH:5][C:4]([CH3:27])=[N:3]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 2723922Sodium ethoxideHCID 69128941N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-(2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzamide

생성물 1

HCID 178428619HCID 178428619, 화합물수율 19%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 8857Ethyl Acetate용매

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온도
78 °C

실험 절차

N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-(2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzamide (as prepared above in Step 4; 0.300 g, 0.793 mmol) was dissolved in anhydrous ethanol (8 mL) and the resulting solution was treated with ethyl formate (0.058 mL, 0.717 mmol) The resulting solution was treated in dropwise fashion with a 21 wt % solution of sodium ethoxide in ethanol (1.48 mL, 3.97 mmol). This reaction mixture was heated at 78° C. for 0.5 h, which caused the reaction mixture to turn black in color. Subsequently, the reaction mixture was cooled to room temperature, and then the reaction pH was adjusted to pH=1 with dropwise addition of 1M HCl(aq). The reaction mixture was diluted with EtOAc (25 mL) and extracted with brine (2×25 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified via flash silica gel chromatography (5% MeOH in CHCl3) affording the title compound in 19% yield (0.061 g, 0.150 mmol).

후처리

  1. temperatureSubsequently, the reaction mixture was cooled to room temperature
  2. extractionextracted with brine (2×25 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified via flash silica gel chromatography (5% MeOH in CHCl3)

출처 및 근거

ORD 기록
ord-1984ca10c1dd4f719a6c315e13e05f91
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07439371B2

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