1,3-Propanediamine → HCID 57718193, 화합물

HRID 1984573노트

반응식

HRID 1984573 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9](Br)=[CH:8][N:7]=[C:6]([NH2:11])[CH:5]=1.[I-:13].[Na+].NC[CH2:17][CH2:18]N.C(O[CH2:24][CH3:25])(=O)C>C(O)CCCC.[Cu](I)I>[CH2:1]([O:2][C:3](=[O:12])[C:4]1[C:9]([I:13])=[CH:8][N:7]=[C:6]([NH2:11])[CH:5]=1)[CH2:17][CH2:18][CH2:24][CH3:25]

참가 물질

7

반응물 4

HCID 4281,3-PropanediamineHCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 25307230Methyl 2-amino-5-bromoisonicotinate

생성물 1

HCID 57718193HCID 57718193, 화합물수율 58%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 62761-Pentanol용매

실험 절차

2-amino-5-bromo-isonicotinic acid methyl ester (1.79 g, 7.75 mmol) was added to a stirred mixture of copper iodide (145 mg, 0.76 mmol), sodium iodide (2.36 g, 15.73 mmol) and 1,3-diaminopropane (0.13 ml, 1.55 mmol) in n-pentanol (20 ml) and heated to reflux overnight. The reaction was cooled to room temperature, ethyl acetate (100 ml) added and washed with NaHCO3 solution (50 ml) and brine (50 ml) before being dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography using ethyl acetate 1/4 hexane as eluent to afford 2-amino-5-iodo-isonicotinic acid pentyl ester as a yellow solid (1.51 g, 58%). 1H NMR (CDCl3): 8.36 (1H, s, py); 6.77 (1H, s, py); 4.50 (2H, br s, NH2); 4.24 (2H, t, OCH2); 1.72 (2H, m, OCH2CH2); 1.32 (4H, m, OCH2CH2CH2CH2CH3); 0.81 (3H, t, CH2CH3).

후처리

  1. temperatureheated
  2. temperatureto reflux overnight
  3. washwashed with NaHCO3 solution (50 ml) and brine (50 ml)
  4. dry with materialbefore being dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-841c0deeed134f70a93dd59be0f96402
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544702B2

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