HCID 58072196, 화합물 → HCID 58072182, 화합물

HRID 1895128노트

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HRID 1895128 반응식
CON(C)[C:4]([C:6]1[C:11](=[O:12])[CH:10]=[CH:9][N:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[N:7]=1)=[O:5].[CH3:24][CH2:25][Mg+].[Br-]>C1COCC1>[C:4]([C:6]1[C:11](=[O:12])[CH:10]=[CH:9][N:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=2)[N:7]=1)(=[O:5])[CH2:24][CH3:25]

참가 물질

4

반응물 2

HCID 58072196HCID 58072196, 화합물HCID 178461630HCID 178461630, 화합물

생성물 1

HCID 58072182HCID 58072182, 화합물수율 74%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a solution of N-methoxy-N-methyl-4-oxo-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxamide (1.20 g, 3.52 mmol) in THF (20 mL) was added EtMgBr (1.0 M in THF, 7.04 mL, 7.04 mmol) at −78° C. under N2. The mixture was stirred at −78° C. for 1 h. The reaction was quenched with saturated NH4Cl aqueous solution at −78° C. The mixture was warmed to room temperature, extracted with EtOAc, dried over Na2SO4, filtered, concentrated in vacuo and purified by column chromatography on silica gel (hexane/EtOAc=50/50 to 0/100) to yield the title compound (767 mg, 74% yield) as a pale yellow solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 1.06 (3H, t, J=7.2 Hz), 2.99 (2H, q, J=7.2 Hz), 6.73 (1H, d, J=8.3 Hz), 7.79-7.88 (2H, m), 8.06-8.17 (2H, m), 8.97 (1H, d, J=8.3 Hz).

후처리

  1. customThe reaction was quenched with saturated NH4Cl aqueous solution at −78° C
  2. temperatureThe mixture was warmed to room temperature
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography on silica gel (hexane/EtOAc=50/50 to 0/100)

출처 및 근거

ORD 기록
ord-6a1347f3eb254f19bb6da123beca98e4
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513251B2

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