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

HRID 1637692ノート

反応式

HRID 1637692 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収率 63%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
120 °C

実験手順

A mixture of 4-chloro-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester (prepared as described in Preparation E, 3.4343 g, 10.74 mmol) and 1-ethyl-propyl-amine (10 ml) in 10 ml of DMSO was heated at 120° C. for 15 hr. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give a yellow solid. The yellow solid was recrystallized with hexane to give 2.519 g (63%) of the title compound of Preparation F as white crystals, mp 106-107.5° C. Anal. for C22H30N2O3 (C,H,N). 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. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto give a yellow solid
  6. customThe yellow solid was recrystallized with hexane
  7. customto give

出典と根拠

ORDレコード
ord-948f0daff0fa4d74bcb855eaab9ab4c0
出典データセット
uspto-grants-2000_03
特許番号
US06043260

反応ノート

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