Pyridine → HCID 89876288, 화합물

HRID 594128

반응식

HRID 594128 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:13][CH2:12][O:11][C:10]2=[O:14])=[N:6][C:7]=1[CH3:8].N1C=CC=CC=1.[CH3:21][C:22]1[C:26]([CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=2)=[C:25]([CH3:39])[O:24][N:23]=1>ClCCl>[CH3:21][C:22]1[C:26]([CH2:27][O:28][C:29]2[CH:30]=[CH:31][C:32]([S:35]([NH:1][C:2]3[C:7]([CH3:8])=[N:6][C:5]([N:9]4[CH2:13][CH2:12][O:11][C:10]4=[O:14])=[CH:4][CH:3]=3)(=[O:37])=[O:36])=[CH:33][CH:34]=2)=[C:25]([CH3:39])[O:24][N:23]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 164907024-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chlorideHCID 898760323-(5-Amino-6-methyl-2-pyridinyl)-1,3-oxazolidin-2-one

생성물 1

HCID 89876288HCID 89876288, 화합물수율 72.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
65 °C

실험 절차

To a solution of 3-(5-amino-6-methyl-2-pyridinyl)-1,3-oxazolidin-2-one (80 mg, 0.414 mmol) in dichloromethane (3 mL) and pyridine (0.033 mL, 0.414 mmol) was added 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (125 mg, 0.414 mmol). The reaction vessel was sealed and heated at 65° C. for 6 hours. The reaction mixture was then allowed to cool and separated between dichloromethane (40 mL) and saturated sodium bicarbonate solution (30 mL). The organic phase was separated using a hydrophobic frit and evaporated in vacuo. The crude was then purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the title compound (137 mg) as a colourless glassy solid. LCMS (2 min, formic) Rt 0.92 min, m/z (ES+) 459 (M+H).

후처리

  1. customThe reaction vessel was sealed
  2. temperatureto cool
  3. customseparated between dichloromethane (40 mL) and saturated sodium bicarbonate solution (30 mL)
  4. customThe organic phase was separated
  5. customevaporated in vacuo
  6. customThe crude was then purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient)
  7. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-6df9302049dd4f26b955ab67804c55e5
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242972B2

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