Diisopropylethylamine → Ethyl (2-methyl-4-{[{5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl}(propyl)amino]methyl}phenoxy)acetate

HRID 1269659노트

반응식

HRID 1269659 반응식
[CH3:1][C:2]1[CH:14]=[C:13]([CH2:15][NH:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C(N(CC)C(C)C)(C)C.Cl[C:30]1[C:35]([CH3:36])=[C:34]([C:37]2[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=2)[N:33]=[CH:32][N:31]=1>C(Cl)Cl>[CH3:1][C:2]1[CH:14]=[C:13]([CH2:15][N:16]([C:30]2[C:35]([CH3:36])=[C:34]([C:37]3[CH:38]=[CH:39][C:40]([C:43]([F:45])([F:46])[F:44])=[CH:41][CH:42]=3)[N:33]=[CH:32][N:31]=2)[CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 184484034-chloro-5-methyl-6-[4-(trifluoromethyl)phenyl]PyrimidineHCID 58622861Ethyl {2-methyl-4-[(propylamino)methyl]phenoxy}acetate

생성물 1

HCID 58622851Ethyl (2-methyl-4-{[{5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl}(propyl)amino]methyl}phenoxy)acetate수율 45.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

A mixture of ethyl {2-methyl-4-[(propylamino)methyl]phenoxy}acetate (0.279 g, 1.05 mmol), N,N-diisopropylethylamine (0.24 mL, 1.4 mmol) and 4-chloro-5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidine (0.191 g, 0.7 mmol) were heated at 100° C. in a sealed reactivial for 18 h. After this time the reactivial was allowed to cool to room temperature and the residue dissolved in CH2Cl2 (50 mL) and washed with water (20 mL). The organic extract was separated by hydrophobic frit and evaporated. Purification by Biotage™ chromatography (Si, 40 g) eluting 9:1 cyclohexane:EtOAc afforded the title compound as a pale yellow oil (159 mg).

후처리

  1. temperatureto cool to room temperature
  2. washwashed with water (20 mL)
  3. extractionThe organic extract
  4. customwas separated by hydrophobic frit
  5. customevaporated
  6. customPurification by Biotage™ chromatography (Si, 40 g)
  7. washeluting 9:1 cyclohexane

출처 및 근거

ORD 기록
ord-d52761d1af5047b6bb76e41a706a60cf
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199239B2

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