Diisopropylethylamine → Ethyl 3-[n-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)methylamino]propionate

HRID 17427ノート

反応式

HRID 17427 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.C(N(C(C)C)CC)(C)C.Cl.[CH3:31][NH:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>ClCCl>[C:19]([C:7]1[C:5]2[N:6]=[C:2]([CH2:31][NH:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[O:3][C:4]=2[C:10]([F:11])=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[CH3:18])#[N:20]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 22629233Ethyl 3-(methylamino)propanoate hydrochlorideHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 68585798Ethyl 3-[n-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)methylamino]propionate収率 81%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (0.49 g, 1.71 mmol), diisopropylethylamine (0.70 ml, 4.12 mmol) and ethyl 3-(methylamino)propionate hydrochloride (I-159) (0.32 g, 1.91 mmol) were dissolved in dichloromethane (15 ml). After heated under reflux for 3 hours, this was diluted with dichloromethane. After washed with water and drying over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=70; 1), then again purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 2:1) to obtain the entitled compound (0.53 g, 81%) as a brown oil.

後処理

  1. temperatureAfter heated
  2. temperatureunder reflux for 3 hours
  3. washAfter washed with water
  4. dry with materialdrying over anhydrous sodium sulfate
  5. customthe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=70; 1)
  7. customagain purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 2:1)

出典と根拠

ORDレコード
ord-e71dad24ae02472486fdc06f7f991ab3
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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