3-Pentanamine → 4-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)nicotinic acid methyl ester

HRID 967964ノート

反応式

HRID 967964 の反応式
[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9](Cl)=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21].[CH2:23]([CH:25]([NH2:28])[CH2:26][CH3:27])[CH3:24]>CS(C)=O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([NH:28][CH:25]([CH2:26][CH3:27])[CH2:23][CH3:24])=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21]

参加物

4

反応物 2

HCID 120193-PentanamineHCID 248056514-Chloro-2-(2,4,6-trimethyl-phenoxy)-6-methyl-nicotinic acid methyl ester

生成物 1

HCID 232165764-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)nicotinic acid methyl ester

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A mixture of 4-chloro-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester (500 mg, 1.56 mmol) and 1-ethyl-propyl-amine (0.8 ml) in 1 ml of DMSO was heated at reflux for 15 hours. The mixture was quenched with sat. ammonium chloride and extracted with ethyl acetate. The organic layer was dried and concentrated to give 445.6 mg of yellow solid. The solid was purified through silica gel column chromatography using 1:1 ratio of chloroform:hexane as eluent to give (289 mg, 50%) of the title compound as white crystals, mp 98-102° C.; 1H NMR (CDCl3) δ 8.04 (d, 1H), 6.85 (s, 2H), 6.06 (s, 1H), 3.85 (s, 3H), 3.32 (m, 1H), 2.28 (s, 3H), 2.10 (s, 3H), 2.07 (s, 3H), 1.62 (m, 4H), 0.95 (t, 6H) ppm.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 15 hours
  3. customThe mixture was quenched with sat. ammonium chloride
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-0c330cd21e7d46839cdf848355b274cc
出典データセット
uspto-grants-2005_10
特許番号
US06956047B1

反応ノート

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