Water → 4-methyl-1-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)-1H-imidazole

HRID 273082노트

반응식

HRID 273082 반응식
[CH3:1][C:2]1[N:3]=[C:4](S)[N:5]([CH2:7][C:8]2([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:16][CH:15]=3)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:6]=1.O>C(O)C.[Ni]>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][C:8]2([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:16][CH:15]=3)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:6]=1

참가 물질

5

반응물 2

HCID 962WaterHCID 178430224HCID 178430224, 화합물

생성물 1

HCID 598375014-methyl-1-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)-1H-imidazole수율 16%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매

실험 절차

4-methyl-1-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)-1H-imidazole-2-thiol (0.6 g, 1.44 mmol) was dissolved in ethanol (20 mL), water (5 mL) was added, and the mixture was cooled in ice. Raney nickel (4 g) was added, the reaction mixture was warmed to room temperature and stirred for 2 hours. The reaction mixture was filtered though Arbocel® and concentrated in vacuo to provide a brown oil. This was purified by flash chromatography on silica gel eluting with ethyl acetate:diethylamine (95:5) to provide the title compound (0.086, 16%) as a clear oil. 1H NMR (400 MHz CDCl3) δ 1.80-1.90 (m, 6H), 2.08-2.18 (m, 7H), 2.65-2.80 (m, 6H), 3.50 (t, 2H), 3.80 (m, 2H), 3.90 (s, 2H), 4.05 (t, 2H), 6.10 (s, 1H), 6.70 (s, 1H), 6.89 (d, 2H), 7.0 (d, 2H). LRMS ESI+ m/z 384 [MH]+.

후처리

  1. temperaturethe mixture was cooled in ice
  2. filtrationThe reaction mixture was filtered though Arbocel®
  3. concentrationconcentrated in vacuo
  4. customto provide a brown oil
  5. customThis was purified by flash chromatography on silica gel eluting with ethyl acetate:diethylamine (95:5)

출처 및 근거

ORD 기록
ord-3157723bf48a4b02a834b61c487e1d6d
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456164B2

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