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Diisopropylethylamine → 2-{6-(4-Chloro-benzyl)-2-[1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-ylamino]-pyrimidin-4-yl}-propan-2-ol

HRID 451434
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인쇄 미리보기

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HRID 451434 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]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[N:16]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1.O>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][C:17]2[N:16]=[C:15]([NH:13][CH:10]3[CH2:9][CH2:8][N:7]([C:5]4[O:6][C:2]([CH3:1])=[N:3][N:4]=4)[CH2:12][CH2:11]3)[N:20]=[C:19]([C:21]([OH:24])([CH3:23])[CH3:22])[CH:18]=2)=[CH:27][CH:28]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 673446221-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-ylamineHCID 866567012-[2-Chloro-6-(4-chloro-benzyl)-pyrimidin-4-yl]-propan-2-ol

생성물 1

HCID 533535252-{6-(4-Chloro-benzyl)-2-[1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-ylamino]-pyrimidin-4-yl}-propan-2-ol

시약·촉매·용매 2

HCID 962Water용매
HCID 312751,4-Dioxane용매

실험 절차

A solution of 1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-ylamine (50 mg, 0.27 mmol), 2-[2-chloro-6-(4-chloro-benzyl)-pyrimidin-4-yl]-propan-2-ol (81.5 mg, 0.27 mmol)) and N,N-diisopropylethylamine (71 L, 0.41 mmol) in dioxane (2.8 mL) was heated at 160° C. in a microwave oven for 6 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 using a gradient from CH2Cl2 to CH2Cl2/MeOH 19:1 (v/v) as eluent. The title compound was obtained as a colorless foam (31 mg, 26%).

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 using a gradient from CH2Cl2 to CH2Cl2/MeOH 19:1 (v/v) as eluent

출처 및 근거

ORD 기록
ord-04d5fe992e4b492aa9872be1102e5467
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08486967B2

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