Diisopropylethylamine → 1-(4-(2-(5-Bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)piperidin-1-yl)ethanone

HRID 1809556노트

반응식

HRID 1809556 반응식
[Br:1][C:2]1[CH:3]=[C:4]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]([NH:8][C:9]([NH2:11])=[S:10])=[N:6][CH:7]=1.[C:19]([N:22]1[CH2:27][CH2:26][CH:25]([C:28](=O)[CH2:29]Br)[CH2:24][CH2:23]1)(=[O:21])[CH3:20].CCN(C(C)C)C(C)C>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:5]([NH:8][C:9]2[S:10][CH:29]=[C:28]([CH:25]3[CH2:26][CH2:27][N:22]([C:19](=[O:21])[CH3:20])[CH2:23][CH2:24]3)[N:11]=2)=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 772303261-(1-Acetylpiperidin-4-yl)-2-bromoethan-1-oneHCID 866314811-(5-Bromo-3-phenoxypyridin-2-yl)thiourea

생성물 1

HCID 249445171-(4-(2-(5-Bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)piperidin-1-yl)ethanone수율 95%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

1-(5-bromo-3-phenoxypyridin-2-yl)thiourea (Example 1, Step E; 30.0 g, 92.5 mmol) and 1-(1-acetylpiperidin-4-yl)-2-bromoethanone (Example 2, Step C, 32.1 g, 130 mmol) were suspended in ethanol (400 mL) and DIEA (48.3 mL, 278 mmol) was added. The resulting mixture was heated to 60° C. for 4 hours and then at ambient temperature overnight. The reaction was concentrated to dryness, dissolved in CH2Cl2 and washed with saturated aqueous sodium bicarbonate, water, dried over Na2SO4, filtered and concentrated. The resulting material was purified on silica eluting with 3% MeOH/EtOAc to give 1-(4-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)piperidin-1-yl)ethanone (41.6 g, 95.0% yield) as a tan solid.

후처리

  1. customat ambient temperature
  2. customovernight
  3. concentrationThe reaction was concentrated to dryness
  4. dissolutiondissolved in CH2Cl2
  5. washwashed with saturated aqueous sodium bicarbonate, water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting material was purified on silica eluting with 3% MeOH/EtOAc

출처 및 근거

ORD 기록
ord-2a62af230fc1401796fc64038f9b279e
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362037B2

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