Pyridine → 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl methoxy(methyl)carbamate

HRID 2424321노트

반응식

HRID 2424321 반응식
[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:16]2[CH2:18][CH2:17]2)=[C:4]([OH:19])[CH:3]=1.N1C=CC=CC=1.[C:26](Cl)(Cl)=[O:27].C1(C)C=CC=CC=1.Cl.[CH3:38][NH:39][O:40][CH3:41]>O.C1(C)C=CC=CC=1>[CH3:41][O:40][N:39]([CH3:38])[C:26](=[O:27])[O:19][C:4]1[CH:3]=[C:2]([Cl:1])[N:7]=[N:6][C:5]=1[O:8][C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH:16]1[CH2:18][CH2:17]1

참가 물질

7

반응물 4

HCID 1049Pyridine2회HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 19083224Phosgen tolueneHCID 178424441HCID 178424441, 화합물

생성물 1

HCID 229401746-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl methoxy(methyl)carbamate수율 38.1%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

200 mg (0.722 mmol) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol was mixed with toluene (3 mL) and the mixture was ice-cooled. To the mixture were added 60 ìL (0.742 mmol) of pyridine, then 0.67 mL (0.724 mmol) of 1.08 mol/L phosgene-toluene solution under nitrogen atmosphere with stirring, and the resulting mixture was stirred at room temperature for 15 minutes. The reaction mixture was ice-cooled, 120 ìL (1.48 mmol) of pyridine, then 70.4 mg (0.722 mmol) of N,O-dimethylhydroxylamine hydrochloride were added to the mixture, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane: ethyl acetate, gradient) to obtain 100 mg (0.275 mmol, Yield: 38.1%) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl methoxy(methyl)carbamate (Compound No. 3564).

후처리

  1. temperaturecooled
  2. temperaturecooled
  3. stirringthe resulting mixture was stirred at room temperature for 1 hour
  4. extractionextracted with ethyl acetate
  5. washwashed successively with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed
  8. customthe obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane: ethyl acetate, gradient)

출처 및 근거

ORD 기록
ord-b71b4d90f4274a5ca79886a96b2655a0
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964531B2

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