Trifluoroacetic acid → 1-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]hexahydro-1H-1,4-diazepine

HRID 419588노트

반응식

HRID 419588 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:19][CH2:18][CH2:17][N:16]([C:20](OC(C)(C)C)=O)[CH2:15][CH2:14]1.C(O)(C(F)(F)F)=O.[CH3:34][S:35]([CH:38]=C)(=[O:37])=[O:36]>C(Cl)Cl.O1CCOCC1>[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:19][CH2:18][CH2:17][N:16]([CH2:20][CH2:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH2:15][CH2:14]1

참가 물질

6

반응물 3

HCID 6422Trifluoroacetic acidHCID 19354Methyl vinyl sulfoneHCID 594527471,1-dimethylethyl 4-[2-methyl-5-(methyloxy)-4-nitrophenyl]hexahydro-1H-1,4-diazepine-1-carboxylate

생성물 1

HCID 598602621-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]hexahydro-1H-1,4-diazepine수율 98%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

반응 조건

온도
30 °C

실험 절차

1,1-Dimethylethyl 4-[2-methyl-5-(methyloxy)-4-nitrophenyl]hexahydro-1H-1,4-diazepine-1-carboxylate (0.7 g, 2.0 mmol) was taken up in 20 mL of DCM and treated with 7 mL of TFA. The mixture stirred for 1 h and was then reduced in vacuo. The solids were transferred to a 50 mL sealed tube and taken up in 20 mL of dioxane. TEA (0.58 g, 5.75 mmol) was added followed by ethenyl methyl sulfone (0.51 g, 4.79 mmol). The mixture was heated to 30° C. for 24 h. The solvent was rotovaped down and the crude product was purified by flash chromatography to give the title compound of step B (0.7 g, 1.88 mmol, 98%). 1H NMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), 6.56 (s, 1H), 3.86 (s, 3H), 3.33-3.42 (m, 4H), 3.26 (t, J=6.68 Hz, 2H), 2.99 (s, 3H), 2.87 (t, J=6.59 Hz, 2H), 2.74-2.81 (m, 2H), 2.67-2.74 (m, 2H), 2.20 (s, 3H), 1.81-1.89 (m, 2H).

후처리

  1. customsealed tube
  2. customthe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-09d4525b81ab43de84b627e64aa38050
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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