1,3-Propanediamine → HCID 57718193、化合物

HRID 1366821ノート

反応式

HRID 1366821 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 57718193HCID 57718193、化合物収率 58%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 62761-Pentanol溶媒

実験手順

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 (1 H, s, py); 6.77 (1 H, s, py); 4.50 (2 H, br s, NH2); 4.24 (2 H, t, OCH2); 1.72 (2 H, m, OCH2CH2); 1.32 (4 H, m, OCH2CH2CH2CH2CH3); 0.81 (3 H, t, CH2CH3).

後処理

  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

出典と根拠

ORDレコード
ord-0b145ad523ed42d09a276ce2f8de7648
出典データセット
uspto-grants-2011_02
特許番号
US07893077B2

反応ノート

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