1-Naphthalenecarbonyl chloride → [3-(2-Morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridin-1-yl]-naphthalen-1-yl-methanone

HRID 1783786

반응식

HRID 1783786 반응식
[C:1]1([C:11](Cl)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-].[Cl-].[Cl-].[Al+3].[N:18]1([CH2:24][CH2:25][C:26]2[N:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]3=[CH:28][N:27]=2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>ClCCCl>[N:18]1([CH2:24][CH2:25][C:26]2[N:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]3=[C:28]([C:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)=[O:12])[N:27]=2)[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1

참가 물질

5

반응물 3

HCID 701461-Naphthalenecarbonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 688300163-(2-Morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine

생성물 1

HCID 24948211[3-(2-Morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridin-1-yl]-naphthalen-1-yl-methanone수율 48%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매2회

실험 절차

To a solution of naphthoylchloride (0.28 mL, 1.85 mmol) in 1,2-dichloroethane (20 mL) was added aluminum trichloride (300 mg, 2.25 mmol). The mixture was allowed to stir for 10 min. then a solution of 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine (200 mg, 0.87 mmol) in 1,2-dichloroethane (5 mL) was added. The mixture was stirred at ambient temperature for 30 min. then washed with saturated aqueous sodium bicarbonate and the organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica to yield the title compound (160 mg, 48%). 1H NMR (DMSO-d6 δ 8.56 (1H), 8.27 (1H), 8.07 (1H), 8.02 (2H), 7.76 (1H), 7.51 (4H), 7.11 (1H), 3.52 (4H), 3.18 (2H), 2.67 (2H), 2.40 (4H); m/z (M+H)=386.2.

후처리

  1. stirringThe mixture was stirred at ambient temperature for 30 min.
  2. washthen washed with saturated aqueous sodium bicarbonate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica

출처 및 근거

ORD 기록
ord-4a2e32fd45894d59a095857b914e8044
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501438B2

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