Triethylamine → 2-(Diethylamino)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17403

反応式

HRID 17403 の反応式
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[F:11])[N:6]=1.Cl.CN.[CH2:24]([N:26](CC)[CH2:27][CH3:28])[CH3:25].C(=O)([O-])O.[Na+]>ClCCl>[CH2:24]([N:26]([CH2:27][CH3:28])[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[F:11])[N:6]=1)[CH3:25]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 6364545Methylamine hydrochlorideHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 685846722-(Diethylamino)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile収率 82%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
45 °C

実験手順

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (100 mg, 0.35 mmol) was dissolved in dichloromethane (5 ml) in a sealed tube, then methylamine hydrochloride (26 mg, 0.38 mmol) and triethylamine (122 μl, 0.87 mmol) were successively added. The reaction system was heated at 45° C. for 3 hours. After cooling to room temperature, the reaction liquid was fractionated with dichloromethane and an aqueous saturated sodium hydrogencarbonate solution. The aqueous layer was separated, this was extracted twice with dichloromethane. The organic layers were combined, washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform) to obtain the entitled compound (80 mg, 82%) as a white solid.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe reaction liquid
  3. customThe aqueous layer was separated
  4. extractionthis was extracted twice with dichloromethane
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe insoluble matter was separated by filtration
  8. customthe solvent was evaporated away
  9. customthe resulting residue was purified by preparative TLC (eluent, chloroform)

出典と根拠

ORDレコード
ord-55af08ed1d3b45459730a9886818e8dd
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

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