Dimethylformamide → N-[5-cyano-2-(4-morpholinyl)-1,3-thiazol-4-yl]-N-(1-phenylethyl)acetamide

HRID 1958034

반응식

HRID 1958034 반응식
[H-].[Na+].[C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:7][C:6]=1[NH:16][C:17](=[O:19])[CH3:18])#[N:4].Br[CH:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:22].CN(C)C=O>O1CCCC1.CCOC(C)=O>[C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:7][C:6]=1[N:16]([CH:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:22])[C:17](=[O:19])[CH3:18])#[N:4]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11454(1-Bromoethyl)benzeneHCID 24758Sodium hydrideHCID 66780286N-[5-cyano-2-(4-morpholinyl)-1,3-thiazol-4-yl]acetamide

생성물 1

HCID 66780432N-[5-cyano-2-(4-morpholinyl)-1,3-thiazol-4-yl]-N-(1-phenylethyl)acetamide수율 84.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

NaH (43.6 mg, 1.090 mmol) was added to a suspension of N-[5-cyano-2-(4-morpholinyl)-1,3-thiazol-4-yl]acetamide (250 mg, 0.991 mmol) in Tetrahydrofuran (THF) (8 mL) at 0° C. The resulting mixture was stirred at 0° C. for 10 min. (1-Bromoethyl)benzene (183 mg, 0.991 mmol) was added dropwise. N,N-Dimethylformamide (DMF) (2 mL) was added. The reaction mixture was heated at 50° C. overnight. LCMS showed the reaction was almost completed. EtOAc was added and washed with H2O, brine and dried (Na2SO4). Removal of the solvent followed by flash column chromatography on a 25 g silica column, which was eluted with 50% EtOAc/hexane to give 300 mg of light yellow sticky/foamy solid as the product.

후처리

  1. additionwas added dropwise
  2. washwashed with H2O, brine
  3. dry with materialdried (Na2SO4)
  4. customRemoval of the solvent
  5. washwas eluted with 50% EtOAc/hexane

출처 및 근거

ORD 기록
ord-f2acc79ef5c34c2494aad2ae5239932e
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410095B2

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