Diisopropylethylamine → 5-[[2-(dimethylamino)-2-oxoethyl](methyl)amino]-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

HRID 897302ノート

反応式

HRID 897302 の反応式
Br[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:13])[C:9]([OH:23])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:24][N:25]([CH3:31])[C:26](=[O:30])[CH2:27][NH:28][CH3:29].C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:24][N:25]([CH3:31])[C:26](=[O:30])[CH2:27][N:28]([CH3:29])[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:13])[C:9]([OH:23])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 2063713N,N-dimethyl-2-(methylamino)acetamideHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

生成物 1

HCID 159582765-[[2-(dimethylamino)-2-oxoethyl](methyl)amino]-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
135 °C

実験手順

Into a 10 mL pressure vessel equipped with a magnetic stir bar was placed 0.1 g (0.266 mmol) 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide (see Example 126), 0.031 g (0.27 mmol) N,N-dimethyl-2-(methylamino)acetamide, 0.726 mL (0.8 mmol) N,N-diisopropylethylamine and 5 mL DMF. The vessel was sealed and heated on an oil bath to 135° C. for 18 hrs., after which the mixture was cooled and the solvent removed in vacuo. The residue was purified by reverse phase HPLC on a C18 column using acetonitrile/water as eluent to give 5-[[2-(dimethylamino)-2-oxoethyl](methyl)amino]-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide.

後処理

  1. customInto a 10 mL pressure vessel equipped with a magnetic stir bar
  2. customThe vessel was sealed
  3. temperature, after which the mixture was cooled
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by reverse phase HPLC on a C18 column

出典と根拠

ORDレコード
ord-f650dd53b06a455094f07ddcb819e93b
出典データセット
uspto-grants-2005_07
特許番号
US06921759B2

反応ノート

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