Diisopropylethylamine → 2-[2-[1-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-ylamino]-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-ol

HRID 451432노트

반응식

HRID 451432 반응식
[CH3:1][C:2]1[O:6][C:5]([N:7]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2)=[N:4][N:3]=1.Cl[C:15]1[N:20]=[C:19]([C:21]([OH:24])([CH3:23])[CH3:22])[CH:18]=[C:17]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[N:16]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1.O>[CH3:1][C:2]1[O:6][C:5]([N:7]2[CH2:8][CH2:9][CH:10]([NH:13][C:15]3[N:20]=[C:19]([C:21]([OH:24])([CH3:23])[CH3:22])[CH:18]=[C:17]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:27][CH:26]=4)[N:16]=3)[CH2:11][CH2:12]2)=[N:4][N:3]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 673446221-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-ylamineHCID 866336402-[2-Chloro-6-(4-trifluoromethyl-phenyl)pyrimidine-4-yl]-propan-2-ol

생성물 1

HCID 533535232-[2-[1-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-ylamino]-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-ol

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A solution of 1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-ylamine (36.5 mg, 0.2 mmol), 2-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-ol (69.1 mg, 0.22 mmol)) and N,N-diisopropylethylamine (52 L, 0.3 mmol) in dioxane (2 mL) was heated at 160° C. in a microwave oven for 5.5 hours. The reaction was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with EtOAc/EtOH 9:1 (v/v) as eluent. The title compound was obtained as a white solid (29 mg, 31%).

후처리

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with saturated aqueous NaCl solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel with EtOAc/EtOH 9:1 (v/v) as eluent

출처 및 근거

ORD 기록
ord-0bef1254584347a796a48a588727f7e6
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486967B2

반응 노트

불러오는 중…