Diisopropylethylamine → benzyl 2-[3-({[4-fluoro-2-(methylsulfonyl)benzyl]amino}carbonyl)-4-hydroxy-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl(methyl)carbamate

HRID 1179318ノート

反応式

HRID 1179318 の反応式
[CH2:1]([O:8][C:9]([N:11]([CH3:30])[CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[C:17]([OH:24])=[C:16]([C:25](OC)=[O:26])[C:15]1=[O:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl-].[F:41][C:42]1[CH:47]=[CH:46][C:45]([CH2:48][NH3+:49])=[C:44]([S:50]([CH3:53])(=[O:52])=[O:51])[CH:43]=1>CO>[F:41][C:42]1[CH:47]=[CH:46][C:45]([CH2:48][NH:49][C:25]([C:16]2[C:15](=[O:29])[N:14]([CH2:13][CH2:12][N:11]([CH3:30])[C:9](=[O:10])[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:23]3[C:18]([C:17]=2[OH:24])=[N:19][CH:20]=[CH:21][CH:22]=3)=[O:26])=[C:44]([S:50]([CH3:53])(=[O:52])=[O:51])[CH:43]=1

参加物

5

反応物 3

HCID 81531Diisopropylethylamine2 回HCID 223464531-[4-fluoro-2-(methylsulfonyl)phenyl]methanaminium ChlorideHCID 58977989Methyl 1-{2-[[(benzyloxy)carbonyl](methyl)amino]ethyl}-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

生成物 1

HCID 58977990benzyl 2-[3-({[4-fluoro-2-(methylsulfonyl)benzyl]amino}carbonyl)-4-hydroxy-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl(methyl)carbamate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

A solution of methyl 1-{2-[[(benzyloxy)carbonyl](methyl)amino]ethyl}-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (0.5 g, 1.21 mmol) in MeOH (6 mL) was treated with Hunig's base (0.33 mL, 1.82 mmol) and 1-[4-fluoro-2-(methylsulfonyl)phenyl]methanaminium chloride (0.35 g, 1.46 mmol) and heated in a sealed reaction vessel at 80 degrees C. After overnight, an additional 0.5 equivalents of the amine and 1.5 equivalents of Hunig's base was added and the reaction heated until HPLC showed the starting material gone. The reaction was cooled and the solids that percipitated were collected by filtration to give pure product.

後処理

  1. temperaturethe reaction heated until HPLC
  2. temperatureThe reaction was cooled
  3. filtrationthe solids that percipitated were collected by filtration
  4. customto give pure product

出典と根拠

ORDレコード
ord-4aec81a40a8141f887e11c34eb4c1a55
出典データセット
uspto-grants-2007_10
特許番号
US07279487B2

反応ノート

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