Sodium Iodide → [Rac]-[4-(methyl-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethyl}-amino)-naphthalen-1-yloxy]-acetic acid ethyl ester

HRID 1726963노트

반응식

HRID 1726963 반응식
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([NH:17][CH3:18])=[CH:9][CH:8]=1)[CH3:2].Cl[CH:21]([C:23]1[C:24]([CH3:39])=[N:25][C:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=2)=[CH:27][CH:28]=1)[CH3:22].[Na+].[I-].C1CCN2C(=NCCC2)CC1>CS(C)=O>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([N:17]([CH3:18])[CH:21]([C:23]2[C:24]([CH3:39])=[N:25][C:26]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=3)=[CH:27][CH:28]=2)[CH3:22])=[CH:9][CH:8]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21935947[Rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridineHCID 69037388(4-Methylamino-naphthalen-1-yloxy)-acetic Acid Ethyl Ester

생성물 1

HCID 69035155[Rac]-[4-(methyl-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethyl}-amino)-naphthalen-1-yloxy]-acetic acid ethyl ester

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
40 °C

실험 절차

0.095 g (0.37 mmol) of the above prepared (4-methylamino-naphthalen-1-yloxy)-acetic acid ethyl ester and 0.220 g of [rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine (see below 1G], 2.0 eq.) were treated in 2.8 ml of DMSO with 0.110 g (1 eq.) of NaI and 0.168 g (1.5 eq.) of DBU. After stirring for 20 h at 40° C., the reaction mixture was poured onto crashed ice/KHSO4, extracted twice with AcOEt, washed with water and brine, and dried over sodium sulfate. Evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=85/15), afforded 0.055 g of the title compound as light brown oil.

후처리

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with AcOEt
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvents

출처 및 근거

ORD 기록
ord-84c7a4ebcd9e47cda2fca6c864dc8c83
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495001B2

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