Dimethylformamide → 6-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide

HRID 2080276ノート

反応式

HRID 2080276 の反応式
Cl[C:2]1[N:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:5].[F:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[CH2:23][CH2:24][NH2:25].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C(OCC)(=O)C>[Cl:18][C:16]1[CH:15]=[CH:14][C:3]([C:4]([NH:6][CH2:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[O:5])=[C:2]([NH:25][CH2:24][CH2:23][C:22]2[CH:26]=[CH:27][CH:28]=[C:20]([F:19])[CH:21]=2)[N:17]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5339282-(3-Fluorophenyl)ethanamineHCID 175874832,6-dichloro-N-(pyridin-3-ylmethyl)pyridine-3-carboxamide

生成物 1

HCID 597382236-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide収率 46%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2,6-dichloro-N-(pyridin-3-ylmethyl)nicotinamide (20.4 g, 72.3 mmol), 3-fluorophenethyl amine (11.1 g, 79.5 mmol), K2CO3 (20 g 145 mmol) and DMF (200 mL) was stirred at 100° C. for 10 hours. The mixture was diluted with ethyl acetate (2×300 mL) and washed with saturated ammonium chloride, sodium bicarbonate and brine. The organic layers were combined, dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography to give 6-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide (12.6 g, 46%). LRMS (M+H+) m/z 385.1.

後処理

  1. washwashed with saturated ammonium chloride, sodium bicarbonate and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-60903f7240f44134907988e09c2c190b
出典データセット
uspto-grants-2011_04
特許番号
US07932270B2

反応ノート

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