Ethanol → 6-[4-(2-Methylamino-ethyl)-phenoxy]-nicotinamide

HRID 130908

反応式

HRID 130908 の反応式
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.Cl[C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(O)C>CN(C)C=O>[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=2)=[CH:7][CH:6]=1

参加物

6

反応物 4

HCID 702EthanolHCID 9727N-MethyltyramineHCID 10796Cesium carbonateHCID 804566-Chloronicotinamide

生成物 1

HCID 597303256-[4-(2-Methylamino-ethyl)-phenoxy]-nicotinamide収率 22.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

Combine 4-(2-methylamino-ethyl)-phenol (1.0 g, 6.6 mmol), 6-chloronicotinamide (1.0 g, 6.6 mmol), and cesium carbonate (4.3 g, 13.2 mmol) in N,N-dimethylformamide (30 mL), stir and heat at 85° C. for 18 hours. Cool to room temperature and evaporate on a rotary evaporator to yield the crude product (1.3 g). The crude product is purified by flash column chromatography on silica gel eluting with 1% conc. ammonium hydroxide/10% ethanol in chloroform then ethanol to yield 6-[4-(2-Methylamino-ethyl)-phenoxy]-nicotinamide (0.4 g, 1.5 mmol): 1H NMR (DMSO-d6, 300.00 MHz): 8.58 (d, 1H); 8.22 (dd, 1H); 7.26-7.23 (m, 2H); 7.05-7.02 (m, 3H); 3.32 (br, 2H); 2.69 (m, 5H); 2.29 (m, 4H)m/z=271.87 (M+1); HPLC=99% (5/95 to 95/5 ACN/(0.1%TFA in water) over 10 minutes, Zorbax SB-Phenyl 4.6 mm×15 cm×5 micron, λ=254 nM.

後処理

  1. temperatureCool to room temperature
  2. customevaporate on a rotary evaporator
  3. customto yield the crude product (1.3 g)
  4. customThe crude product is purified by flash column chromatography on silica gel eluting with 1% conc. ammonium hydroxide/10% ethanol in chloroform

出典と根拠

ORDレコード
ord-9b7cca368c164d29a09aa7e9f915a85b
出典データセット
uspto-grants-2008_06
特許番号
US07381719B2

関連ノート

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