Sodium Carbonate → Benzonitrile, 4-(2-(2-((2r)-2-methyl-1-pyrrolidinyl)ethyl)-5-benzofuranyl)-

HRID 494760노트

반응식

HRID 494760 반응식
CS(O[CH2:6][CH2:7][C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=3)=[CH:13][C:11]=2[CH:12]=1)(=O)=O.Br.[CH3:26][C@@H:27]1[CH2:31][CH2:30][CH2:29][NH:28]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:26][C@@H:27]1[CH2:31][CH2:30][CH2:29][N:28]1[CH2:6][CH2:7][C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=3)=[CH:13][C:11]=2[CH:12]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 113936782-[5-(4-cyanophenyl)-1-benzofuran-2-yl]ethyl MethanesulfonateHCID 12444175(2R)-2-methylpyrrolidine hydrobromide

생성물 1

HCID 9818903Benzonitrile, 4-(2-(2-((2r)-2-methyl-1-pyrrolidinyl)ethyl)-5-benzofuranyl)-수율 35.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

A suspension of Example 1C (0.19 g, 0.55 mmol), (2R)-2-methylpyrrolidine hydrobromide (0.17 g, 1.0 mmol) and sodium carbonate (0.23 g, 2.2 mmol) in acetonitrile (0.4 mL) was heated to 50° C. with stirring for 48 hours. The reaction was cooled to ambient temperature, diluted with acetonitrile and centrifuged. The supernatant liquid was removed and the solids washed with acetonitrile. The combined liquids were concentrated under reduced pressure and the residue chromatographed by reverse phase HPLC with aqueous CF3CO2H/acetonitrile to give the titled compound (0.065 g, 34%). 1H NMR (300 MHz, CD3OD) δ 7.88 (m, 1H), 7.71 (m, 4H), 7.50 (m, 2H), 6.82 (s, 1H), 3.72-3.9 (m, 2H), 3.58 (m, 1H), 3.25-3.5 (m, 4H), 2.48 (m, 1H), 2.05-2.2 (m, 2H), 1.75 (m, 1H), 1.50 (d, J=6 Hz, 3H); MS (DCI) m/z 331 (M+H)+;

후처리

  1. customThe supernatant liquid was removed
  2. washthe solids washed with acetonitrile
  3. concentrationThe combined liquids were concentrated under reduced pressure
  4. customthe residue chromatographed by reverse phase HPLC with aqueous CF3CO2H/acetonitrile

출처 및 근거

ORD 기록
ord-70fa409b6b1b46fb8fafbedb59b1f853
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538138B2

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