Triethylamine → HCID 68465987, 화합물

HRID 507548노트

반응식

HRID 507548 반응식
[Br:1][C:2]1[C:3]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][C:16]([O:18][CH2:19][C@@H:20]4[CH2:24][CH2:23][CH2:22][N:21]4[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:17][C:11]=3[CH:10]=2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:32][CH2:33][CH2:34][N:35]1[C:39]([CH3:41])([CH3:40])[C:38](=[O:42])[NH:37][C:36]1=[O:43].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][C:16]([O:18][CH2:19][C@@H:20]4[CH2:24][CH2:23][CH2:22][N:21]4[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:17][C:11]=3[CH:10]=2)=[N:4][C:5]([NH:32][CH2:33][CH2:34][N:35]2[C:39]([CH3:40])([CH3:41])[C:38](=[O:42])[NH:37][C:36]2=[O:43])=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 574288041-(2-Aminoethyl)-5,5-dimethylimidazolidine-2,4-dioneHCID 86614159HCID 86614159, 화합물

생성물 1

HCID 68465987HCID 68465987, 화합물수율 68.2%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of (2S)-tert-butyl 2-((2-(5-bromo-2-chloropyrimidin-4-yl)benzo[b]thiophen-5-yloxy)methyl)pyrrolidine-1-carboxylate (524 mg, 1.00 mmol) in toluene (25 mL) was treated with 1-(2-aminoethyl)-5,5-dimethylimidazolidine-2,4-dione (205 mg, 1.20 mmol) and triethylamine (121 mg, 1.2 mmol) and then heated to reflux in an oil bath for 3 h. The reaction was cooled to room temperature, diluted with ethyl acetate (25 mL) and washed in turn with a saturated aqueous solution of sodium bicarbonate (15 mL), deionized water (15 mL), and a saturated aqueous solution of sodium chloride (15 mL). The organic layer was separated, dried over sodium sulfate (300 mg), filtered through a coarse frit (to remove the sodium sulfate), and condensed in vacuo to give a white solid (450 mg). The crude material was purified by flash chromatography (EtOAc/hexane v/v) to yield the title compound as a white solid (325 mg, 50%). MS (M+H)+ 659/661.

후처리

  1. temperatureheated
  2. temperatureto reflux in an oil bath for 3 h
  3. washwashed in turn with a saturated aqueous solution of sodium bicarbonate (15 mL), deionized water (15 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate (300 mg)
  6. filtrationfiltered through a coarse frit (
  7. customto remove the sodium sulfate), and
  8. customcondensed in vacuo

출처 및 근거

ORD 기록
ord-f94f9b351ae14848a4afaf98d8c9d88a
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786132B2

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