Hydrochloric Acid → Hydrochloric Acid

HRID 2244527노트

반응식

HRID 2244527 반응식
Br[CH:2]([CH3:34])[C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8](=[O:33])[N:9]([CH:16]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH2:31][CH3:32])[CH:23]=1)[CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:10]2=[O:15])=[O:4].[CH3:35][NH:36][CH3:37].CO.[ClH:40].CCOCC>C(#N)C.C(Cl)Cl.C(=O)([O-])O.[Na+].C(OCC)(=O)C>[CH3:35][N:36]([CH3:37])[CH:2]([CH3:34])[C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8](=[O:33])[N:9]([CH:16]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH2:31][CH3:32])[CH:23]=1)[CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:10]2=[O:15])=[O:4].[ClH:40]

참가 물질

11

반응물 5

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 887MethanolHCID 3283Diethyl EtherHCID 187583882-bromo-N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxoisoindolin-4-yl}propanamide

생성물 2

HCID 313Hydrochloric Acid수율 58%HCID 187583262-(Dimethylamino)-n-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methyl-sulfonyl)ethyl]-1,3-dioxoisoindolin-4-yl}propanamide

시약·촉매·용매 4

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a suspension of 2-bromo-N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxoisoindolin-4-yl}propanamide (500 mg, 0.9 mmol) in acetonitrile (5 mL) was added dimethylamine in methanol (1.5 mL, 2M, 3.0 mmol) at room temperature and the mixture was stirred for 2 days. The mixture was diluted with methylene chloride (50 mL) and sodium hydrogen carbonate (25 mL). The organic layer was separated, washed with brine (25 mL), and dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. To a solution of the oil in ethyl acetate (20 mL) was added hydrogen chloride in ether (1.5 mL, 1N hydrogen chloride, 1.5 mmol). The resulting suspension was filtered and washed with ethyl acetate (10 mL) to give 2-(dimethylamino)-N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxoisoindolin-4-yl}propanamide, hydrogen chloride as a white solid (290 mg, 58% yield): mp, 138-140° C.; 1H NMR (DMSO-d6) δ 1.32 (t, J=6.9 Hz, 3H, CH3), 1.56 (brs, 3H, CH3), 2.83 (brs, 6H, CH3), 3.01 (s, 3H, CH3), 3.73 (s, 3H, CH3), 4.02 (q, J=6.9 Hz, 2H, CH2), 4.15 (dd, J=4.4, 14.2 Hz, 1H, CHH), 4.27 (s, 1H, CH), 4.34 (dd, J=10.6, 14.3 Hz, 1H, CHH), 5.78 (dd, J=4.3, 10.3 Hz, 1H, NCH), 6.91-6.99 (m, 2H, Ar), 7.72 (d, J=7.1 Hz, 1H<Ar), 7.87 (d, J=7.5 Hz, 1H, Ar), 8.14 (m, 1H, Ar), 10.4(brs, 1H, HCl), 10.71 (s, 1H, NH); 13C NMR (DMSO-d6) ε 13.42, 14.67, 41.07, 41.47, 47.31, 52.98, 55.51, 52.74, 63.84, 111.75, 112.31, 119.70, 120.16, 128.92, 129.47, 131.80, 134.05, 135.87, 147.87, 148.91, 166.66, 166.86, 167.65, 168.53; Anal Calcd for C25H31N3O7S+1.1 HCl+0.6 H2O: C, 52.82; H, 5.90; N, 7.39 Cl, 6.86, H2O, 1.90. Found: C, 52.57; H, 5.77; N, 7.10; Cl, 6.90; H2O, 1.47.

후처리

  1. customThe organic layer was separated
  2. washwashed with brine (25 mL)
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customto give an oil
  6. filtrationThe resulting suspension was filtered
  7. washwashed with ethyl acetate (10 mL)

출처 및 근거

ORD 기록
ord-3ac55b84880744aba4648604f6c282ab
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678825B2

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