Triethylamine → HCID 178514319, 화합물

HRID 241985

반응식

HRID 241985 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[CH2:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])=[N:9]1.C(N(CC)CC)C.C(NC1C=CC(S([N:41]=[N+:42]=[N-])(=O)=O)=CC=1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>C(#N)C>[N+:41](=[C:11]1[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])=[N:9][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[C:12]1=[O:13])=[N-:42]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 51291854-Acetamidobenzenesulfonyl azideHCID 671115152,5-bis(2-fluorophenyl)-2,4-dihydro-3H-pyrazol-3-one

생성물 1

HCID 178514319HCID 178514319, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

2,5-Bis(2-fluorophenyl)-2,4-dihydro-3H-pyrazol-3-one (0.63 g, 2.3 mmol) was suspended in acetonitrile (10 mL), treated with triethylamine (0.27 mL, 2.7 mmol, 1.15 equiv) and cooled to 0° C. To the mixture was added 4-acetamidobenzenesulfonyl azide (0.61 g, 2.5 mmol, 1.1 equiv) and after 30 minutes at 0° C., the mixture was warmed to ambient temperature. After stirring for 30 minutes, the mixture was poured into sodium carbonate (25 mL, aqueous saturated) and sodium hydroxide (10 mL, 1 N aqueous) and extracted with dichloromethane (2×125 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate), providing the titled compound.

후처리

  1. temperaturethe mixture was warmed to ambient temperature
  2. extractionextracted with dichloromethane (2×125 mL)
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-13330aa7ae1241b9859f6e898ba7df00
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653079B2

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