Pyridine → HCID 89876288、化合物

HRID 594128

反応式

HRID 594128 の反応式
[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

参加物

5

反応物 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

生成物 1

HCID 89876288HCID 89876288、化合物収率 72.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6df9302049dd4f26b955ab67804c55e5
出典データセット
uspto-grants-2016_01
特許番号
US09242972B2

関連ノート

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