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

HRID 17427노트

반응식

HRID 17427 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e71dad24ae02472486fdc06f7f991ab3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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