Sodium Iodide → {4-[1-(4-Chloro-phenyl)-cyclohexyl]-thiazol-2-yl}-(3-morpholin-4-yl-propyl)-amine

HRID 47277노트

반응식

HRID 47277 반응식
Cl[CH2:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=O.[I-].[Na+].[O:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][NH:29][C:30]([NH2:32])=[S:31])[CH2:22][CH2:21]1>CC(C)=O.C(=O)([O-])O.[Na+].O>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:5]2([C:3]3[N:32]=[C:30]([NH:29][CH2:28][CH2:27][CH2:26][N:23]4[CH2:22][CH2:21][O:20][CH2:25][CH2:24]4)[S:31][CH:2]=3)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:12][CH:13]=1

참가 물질

7

반응물 3

HCID 5238Sodium IodideHCID 2760135N-[3-(4-Morpholinyl)propyl]thioureaHCID 219923432-Chloro-1-[1-(4-chloro-phenyl)-cyclohexyl]-ethanone

생성물 1

HCID 21992318{4-[1-(4-Chloro-phenyl)-cyclohexyl]-thiazol-2-yl}-(3-morpholin-4-yl-propyl)-amine

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
50 °C

실험 절차

A solution of 2-chloro-1-[1-(4-chloro-phenyl)-cyclohexyl]-ethanone (191.5 mg, 0.71 mmol) and sodium iodide (105.8 mg, 0.71 mmol) in acetone (5 mL) was stirred at room temperature for 10 min. Next, 1-(3-morpholinopropyl)-2-thiourea (143.6 mg, 0.71 mmol) was added. The resulting mixture was heated at 50° C. overnight. After the mixture was allowed to cool to room temperature, it was diluted with 5% sodium hydrogen carbonate in water and then extracted with ethyl acetate (3×20 mL). The extracts were combined, and dried over anhydrous sodium sulfate, filtered and concentrated to give an oil. The crude was purified by column chromatography on silica gel using dichloromethane/2 N ammonia in ethanol (95:5) to give {4-[1-(4-chloro-phenyl)-cyclohexyl]-thiazol-2-yl}-(3-morpholin-4-yl-propyl)-amine, 94, as an oil (187.1 mg, 63%). 1H (CDCl3, 300 MHz) δ 7.31-7.21 (m, 4H), 6.01 (s, 1H), 5.93 (s, 1H), 3.70-1.52 (m, 24H) ppm;13C (C6D6, 75 MHz) δ 23.5, 25.5, 26.9, 36.7, 45.7, 46.4, 54.2, 57.7, 67.4, 101.3, 128.8, 129.4, 132.0, 146.8, 160.1, 169.5 ppm.

후처리

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe crude was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-a8e36bf78fc84311a1696c8d9b0a7bc2
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699866B2

반응 노트

불러오는 중…